Compound for organic electric element, organic electric element comprising the same and electronic device thereof

ABSTRACT

The present invention provides the compound represented by Formula 1, an organic electric element comprising a first electrode, a second electrode, and an organic material layer formed between the first electrode and the second electrode, and electronic device thereof, and by comprising the compound represented by Formula 1 in the organic material layer, the driving voltage of the organic electronic device can be lowered, and the luminous efficiency and life time of the organic electronic device can be improved.

CROSS-REFERENCE TO RELATED APPLICATION

This patent application claims priority from and the benefit under 35U.S.C. § 119 to § 121, and § 365 of Korean Patent Application No.10-2016-0075404, filed on Jun. 17, 2016, which is hereby incorporated byreference for all purposes as if fully set forth herein. Further, thisapplication claims the benefit of priority in countries other than U.S.,which is hereby incorporated by reference herein.

BACKGROUND Technical Field

The present invention relates to compounds for organic electricelements, organic electric elements comprising the same, and electronicdevices thereof.

Background Art

In general, an organic light emitting phenomenon refers to a phenomenonin which electric energy is converted into light energy of an organicmaterial. An organic electric element utilizing the organic lightemitting phenomenon usually has a structure including an anode, acathode, and an organic material layer interposed therebetween. In manycases, the organic material layer has a multi-layered structure havingrespectively different materials in order to improve efficiency andstability of an organic electric element, and for example, may include ahole injection layer, a hole transport layer, a light emitting layer, anelectron transport layer, an electron injection layer, or the like.

Materials used as an organic material layer in an organic electricelement may be classified into a light emitting material and a chargetransport material, for example, a hole injection material, a holetransport material, an electron transport material, an electroninjection material, and the like according to its function.

Currently, the power consumption is required more and more as size ofdisplay becomes larger and larger in the portable display market.Therefore, the power consumption is a very important factor in theportable display with a limited power source of the battery, andefficiency and life span issue also must be solved.

Efficiency, life span, driving voltage, and the like are correlated witheach other. For example, if efficiency is increased, then drivingvoltage is relatively lowered, and the crystallization of an organicmaterial due to Joule heating generated during operation is reduced asdriving voltage is lowered, as a result of which life span shows atendency to increase. However, efficiency cannot be maximized only bysimply improving the organic material layer. This is because long lifespan and high efficiency can be simultaneously achieved when energylevels and T1 values among the respective layers included in the organicmaterial layer, inherent material properties (mobility, interfacialproperties, etc.) and the like are optimal combination.

Further, an emission-auxiliary layer must be present between the holetransport layer and the light emitting layer in order to solve theproblem of luminescence in the hole transport layer of recent organicelectroluminescent devices, and it is time to develop differentemission-auxiliary layers according to respective light emitting layers(R, G, B).

In general, an electron is transferred from an electron transport layerto a light emitting layer and a hole is transferred from a holetransport layer to the light emitting layer, as a result, an exciton isformed by the recombination of the electron and hole.

However, material used in a hole transport layer has a low T1 valuebecause the material should have a low HOMO value. As a result, theexciton generated in the light emitting layer is transferred to theinterface of the hole transport layer or the hole transport layer, andthereby emitting light at the interface of the hole transport layer or acharge unbalance in the light-emitting layer.

When light is emitted from the interface of the hole transporting layer,the color purity and efficiency of the organic electronic element arelowered and the lifetime is shortened. Therefore, it is strongly desiredto develop materials for the emission-auxiliary layer having a HOMOlevel between the HOMO energy level of the hole transporting layer andthe HOMO energy level of the light emitting layer, a high T1 energyvalue and a hole mobility within a suitable driving voltage range(within a driving voltage range of blue element of a full device).

However, this cannot be achieved simply by the structural properties ofthe core of the emission-auxiliary layer material. An element having ahigh efficiency and a long life span can be realized when thecharacteristics of core and sub-substituents of the emission-auxiliarylayer material, the proper combination of the emission-auxiliary layerand the hole transport layer, and the proper combination of theemission-auxiliary layer and the light emitting layer.

On the other hand, it is also necessary to develop a holeinjection/transport layer materials and an emission-auxiliary layermaterial having stable characteristics against Joule heat generated,that is, a high glass transition temperature when the element is driven.

It has been reported that the low glass transition temperature of thehole transporting layer and the emission-auxiliary layer material lowersthe uniformity of the surface when the device is driven and causes thematerial to deform due to heat generated when the device is driven, as aresult, the life span of the device is greatly affected.

Amine compound comprising a carbazole is very different in propertiesdepending on the material structure, and thus it applies to a holetransport layer and an emission-auxiliary layer as material of anorganic material layer. In particular, band gap (HOMO, LUMO), electricalproperties, chemical properties, physical properties and the like aredepending on the bonding position, number and the introduction ofvarious linker of an amine group bonded to carbazole, and thusdevelopment to apply it to the hole transport layer and anemission-auxiliary layer has been proceeding so far.

As a representative example, the following Patent Documents 1 to 11disclose the performance of an amine compound including a carbazole.

1. JP 2005-154421 A

2. JP 4458361 B2

3. JP 5085842 B2

4. JP 4589223 B2

5. JP 5032016 B2

6. JP 4975318 B2

7. JP 5082356 B2

8. JP 5585044 B2

9. KR 10-1462070 B1

10. KR 10-1627583 B1

11. KR 10-1627584 B1

Patent Documents 1 to 7 disclose a structure in which amines are bondedat the 3-position of carbazole. Since the 3-position of the carbazole isthe para position of the nitrogen atom being an electron donor, theamino group substituted at the 3-position is activated by the nitrogenatom of the carbazole ring. That is, the compound having an amino groupintroduced into the 3-position of the carbazole has a lower ionizationpotential than an ordinary amine compound. Therefore, the hole injectionbarrier in the light emitting layer becomes large, which causes aproblem that the driving voltage increases when the device is driven.

Patent Document 8 discloses a structure in which an amine is bonded atthe 2-position of carbazole, and it is reported that the amine is likelyto have a more appropriate ionization potential when the amine is bondedat 2-position than 3-position of the carbazole. However, it disclosesonly a use example for material in which a carbazole and an amine aredirectly bonded, and a performance characteristic due to introduction oflinker between carbazole and amine cannot be confirmed by PatentDocument 8.

Patent Documents 9 to 11 disclose a structure in which a linking groupis introduced between a carbazole and an amine and is bonded to a2-position of the carbazole, and Patent Documents 9 to 11 disclose theperformance according to the type of the linker and the type of bonding(linear, non-linear).

However, it is still required to develop a hole transport layer and anemission-auxiliary layer materials for an organic electric device havinghigh light emitting efficiency while exhibiting stability such asdurability and heat resistance characteristics in process of the devicedeposition. Therefore, it is necessary to develop materials in thedirection of improving luminous efficiency and lifetime by introducingvarious linking groups and amine substituents while increasing thenumber of amines in existing skeletons based on the compound disclosedin the prior art.

Object, Technical Solution and Effects of the Invention

The object of the present invention is to provide a compound having theefficient electron blocking ability and the hole transporting ability,the high luminous efficiency and the low driving voltage of the device,and the high heat resistance, capable of improving color purity andlifespan, an organic electric element comprising the same, and anelectronic device thereof.

In accordance with an aspect of the present invention, the compoundrepresented by the following formula is provided.

In another aspect of the present invention, organic electric elementcomprising the compound represented by the above formula and anelectronic device including the organic electric element are provided.

According to the present invention, by using a specific compound havingthe carbazole core and the compound in which the kind of the aminegroup, the bonding position of the amine group, and the number of aminegroups are specified, the hole transfer ability and the thermalstability of the organic electric device can be improved, and it has ahigh HOMO energy level, a high T1 value and a high refractive index,which are easy to achieve charge balance in the light emitting layer,and thus the luminous efficiency, the heat resistance, lifetime and thelike the organic electric device can be improved and the driving voltageis lowered.

BRIEF DESCRIPTION OF THE DRAWINGS

The FIGURE illustrates an example of an organic light emitting diodeaccording to an embodiment of the present invention: 100 is organicelectric element, 110 is substrate, 120 is first electrode, 130 is holeinjection layer, 140 is hole transport layer, 141 is buffer layer, 150is light emitting layer, 151 is emission-auxiliary layer, 160 iselectron transport layer, 170 is electron injection layer, and 180 issecond electrode.

DETAILED DESCRIPTION

Hereinafter, some embodiments of the present invention will be describedin detail with reference to the accompanying illustrative drawings.

In designation of reference numerals to components in respectivedrawings, it should be noted that the same elements will be designatedby the same reference numerals although they are shown in differentdrawings. Further, in the following description of the presentinvention, a detailed description of known functions and configurationsincorporated herein will be omitted when it may make the subject matterof the present invention rather unclear.

In addition, terms, such as first, second, A, B, (a), (b) or the likemay be used herein when describing components of the present invention.Each of these terminologies is not used for defining an essence, orderor sequence of a corresponding component but used merely to distinguishthe corresponding component from other component(s). It should be notedthat if it is described in the specification that one component is“connected,” “coupled” or “joined” to another component, a thirdcomponent may be “connected,” “coupled,” and “joined” between the firstand second components, although the first component may be directlyconnected, coupled or joined to the second component.

In addition, it will be understood that when an element such as a layer,film, region or substrate is referred to as being “on” or “over” anotherelement, it can be directly on the other element or intervening elementsmay also be present. In contrast, when an element is referred to asbeing “directly on” another element, there are no intervening elementspresent.

As used in the specification and the accompanying claims, unlessotherwise stated, the following is the meaning of the term as follows.

Unless otherwise stated, the term “halo” or “halogen” as used hereinincludes fluorine (F), bromine (Br), chlorine (Cl), or iodine (I).

Unless otherwise stated, the term “alkyl” or “alkyl group” as usedherein has a single bond of 1 to 60 carbon atoms, and means thesaturated aliphatic functional radicals including a linear alkyl group,a branched chain alkyl group, a cycloalkyl group (alicyclic), acycloalkyl group substituted with an alkyl group and an alkyl groupsubstituted with a cycloalkyl.

Unless otherwise stated, the term “halo alkyl” or “halogen alkyl” asused herein includes an alkyl group substituted with a halogen.

Unless otherwise stated, the term “alkenyl” or “alkynyl” as used hereinhas, but not limited to, double or triple bonds of 2 to 60 carbon atoms,and includes a linear alkyl group, or a branched chain alkyl group.

Unless otherwise stated, the term “cycloalkyl” as used herein means, butnot limited to, alkyl forming a ring having 3 to 60 carbon atoms.

Unless otherwise stated, the term “alkoxyl group”, “alkoxy group” or“alkyloxy group” as used herein means an oxygen radical attached to analkyl group, but not limited to, and has 1 to 60 carbon atoms.

Unless otherwise stated, the term “aryloxyl group” or “aryloxy group” asused herein means an oxygen radical attached to an aryl group, but notlimited to, and has 6 to 60 carbon atoms.

Unless otherwise stated, the term “fluorenyl group” or “fluorenylenegroup” as used herein means univalent or bivalent functional group inwhich R, R′ and R″ are all hydrogen in the following structure,“substituted fluorenyl group” or “substituted fluorenylene group” meansthat at least any one of R, R′ and R″ is a substituent other thanhydrogen, and it comprises the case where R and R′ are bonded to eachother to form the spiro compound together with the carbon to which theyare bonded.

Unless otherwise stated, the term “aryl group” or “arylene group” asused herein has, but not limited to, 6 to 60 carbon atoms. The arylgroup or arylene group include a monocyclic rings, ring assemblies,fused polycyclic system or spiro compounds.

Unless otherwise stated, the term “heterocyclic group” as used hereinmeans, but not limited to, a non-aromatic ring as well as an aromaticring like “heteroaryl group” or “heteroarylene group”. The heterocyclicgroup as used herein means, but not limited to, a ring containing one ormore heteroatoms, and having 2 to 60 carbon atoms. Unless otherwisestated, the term “heteroatom” as used herein represents N, O, S, P orSi. The heterocyclic group means a monocyclic, ring assemblies, fusedpolycyclic system or spiro compound containing one or more heteroatoms.

Also, the term “heterocyclic group” may comprise a ring including SO₂instead of carbon consisting of a ring. For example, “heterocyclicgroup” includes the following compound.

The term “ring” as used herein means, a monocyclic and polycyclic, analiphatic ring and heterocyclic group containing at least oneheteroatom, and an aromatic ring and a non-aromatic ring.

The term “polycyclic ring” as used herein may comprise ring assembliessuch as biphenyl and terphenyl, fused polycyclic system and a spirocompound, an aromatic ring and a non-aromatic ring, and an aliphaticring and heterocyclic group containing at least one heteroatom.

The term “ring assemblies” as used herein means, two or more cyclicsystems (single rings or fused systems) which are directly joined toeach other by double or single bonds are named ring assemblies when thenumber of such direct ring junctions is one less than the number ofcyclic systems involved. The ring assemblies also mean, same ordifferent ring systems are directly joined to each other by double orsingle bonds.

The term “fused polycyclic system” as used herein means, fused ring typewhich has at least two atoms as the common members, fused two or morealiphatic ring systems and a fused hetero ring system containing atleast one heteroatom. Fused polycyclic system is an aromatic ring, ahetero aromatic ring, an aliphatic ring, or a combination thereof.

The term “spiro compound” as used herein has, a spiro union which meansunion having one atom as the only common member of two rings. The commonatom is designated as ‘spiro atom’. The compounds are defined as‘monospiro-’, ‘dispiro-’ or ‘trispiro-’ depending on the number of spiroatoms in one compound.

Also, when prefixes are named subsequently, it means that substituentsare listed in the order described first. For example, an arylalkoxymeans an alkoxy substituted with an aryl, an alkoxylcarbonyl means acarbonyl substituted with an alkoxyl, and an arylcarbonylalkenyl alsomeans an alkenyl substitutes with an arylcarbonyl, wherein thearylcarbonyl may be a carbonyl substituted with an aryl.

Unless otherwise stated, the term “substituted or unsubstituted” as usedherein means that substitution is carried out by at least onesubstituent selected from the group consisting of, but not limited to,deuterium, halogen, an amino group, a nitrile group, a nitro group, aC₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, a C₁-C₂₀ alkylamine group, aC₁-C₂₀ alkylthiophene group, a C₆-C₂₀ arylthiophene group, a C₂-C₂₀alkenyl group, a C₂-C₂₀ alkynyl group, a C₃-C₂₀ cycloalkyl group, aC₆-C₂₀ aryl group, a C₆-C₂₀ aryl group substituted by deuterium, aC₈-C₂₀ arylalkenyl group, a silane group, a boron group, a germaniumgroup, a fluorenyl group, and a C₂-C₂₀ heterocyclic group containing atleast one heteroatom selected from the group consisting of O, N, S, Si,and P.

A ‘group name’ comprised in an aryl group, an arylene group, aheterocyclic group and the like as example of each symbol and asubstituent as used herein may be written in the name of functionalgroup reflecting the valence, and may also be described as the name of aparent compound. For example, in the case of phenanthrene which is akind of aryl group, it may be described by distinguishing valence suchas ‘phenanthryl (group)’ when it is ‘monovalent group’, and as‘phenanthrylene (group)’ when it is ‘divalent group’, and it may also bedescribed as a parent compound name, ‘phenanthrene’, regardless of itsvalence. Similarly, in the case of pyrimidine, it may be described as‘pyrimidine’ regardless of its valence, and it may also be described asthe name of corresponding functional group such as pyrimidinyl (group)when it is ‘monovalent group’, and as ‘pyrimidylene (group)’ when it is‘divalent group’.

Otherwise specified, the formulas used in the present invention are asdefined in the index definition of the substituent of the followingformula.

Wherein, when a is an integer of zero, the substituent R¹ is absent,that is, hydrogen atoms are bonded to all the carbon constituting thebenzene ring, and chemical formulas or compounds may be written withoutexplicitly describing the hydrogen. In addition, one substituent R¹ isbonded to any carbon of the carbons forming the benzene ring when “a” isan integer of 1. When “a” is an integer of 2 or 3, for example,substituents R¹s are bonded to the carbon of the benzene ring asfollowings. Also, substituents R¹s are bonded to the carbon of thebenzene ring when “a” is an integer of 4 to 6 in a similar manner.Further, when “a” is an integer of 2 or more, R¹s may be the same ordifferent from each other.

The FIG. illustrates an organic electric element according to anembodiment of the present invention.

Referring to the FIGURE, an organic electric element 100 according to anembodiment of the present invention includes a first electrode 120formed on a substrate 110, a second electrode 180, and an organicmaterial layer formed between the first electrode 120 and the secondelectrode 180 and comprising the compound of the present invention.Here, the first electrode 120 may be an anode (positive electrode), andthe second electrode 180 may be a cathode (negative electrode). In thecase of an inverted organic electric element, the first electrode may bea cathode, and the second electrode may be an anode.

The organic material layer may include a hole injection layer 130, ahole transport layer 140, a light emitting layer 150, an electrontransport layer 160, and an electron injection layer 170 formed insequence on the first electrode 120. Here, at least one layer of theorganic material layer may be omitted, or the organic material layer mayfurther include a hole blocking layer, an electron blocking layer, anemission-auxiliary layer 151, the electron transport-auxiliary layer, abuffer layer 141, etc., the electron transport layer 160 or the like mayserve as the hole blocking layer, and a hole transport layer 140 and anelectron transport layer 160 are each formed as one or more layers.

Although not shown, the organic electric element according to anembodiment of the present invention may further include a protectivelayer or a layer (Capping layer) for improving luminous efficiencyformed on at least one side of sides of the first electrode and thesecond electrode, wherein at least one side is not facing the organicmaterial layer.

The inventive compound employed in the organic material layer may beused as a material of a hole injection layer 130, a hole transport layer140, an emission-auxiliary layer 151, an electron transport auxiliarylayer, an electron transport layer 160, an electron injection layer 170,as host or dopant of a light emitting layer 150, or as a material of alayer for improving luminous efficiency. For example, the inventivecompound may be used as material of the light emitting layer 150, thehole transport layer 140 and/or the emission-auxiliary layer 151.

On the other hand, even if the core is the same core, the band gap, theelectrical characteristics, the interface characteristics and the likemay be different depending on which substituent is bonded at whichposition. Therefore, it is necessary to study the selection of the coreand the combination of the core and the sub-substituent bonded to thecore. In particular, long life span and high efficiency can besimultaneously achieved when the optimal combination of energy levelsand T₁ values, inherent material properties (mobility, interfacialproperties, etc.), and the like among the respective layers of anorganic material layer is achieved.

As already described above, generally, in order to solve the emissionproblem with a hole transport layer of an organic electric element, itis preferable that an emission-auxiliary layer is formed between thehole transport layer and a light emitting layer, and it is necessary todevelop different emission-auxiliary layers according to respectivelight emitting layers (R, G, B). On the other hand, even if the core ofan emission-auxiliary layer is similar, it is very difficult to inferthe characteristics of an emission-auxiliary layer because it isnecessary to grasp the correlation between the emission-auxiliary layerand a hole transport layer and a light emitting layer (host).

Therefore, according to the present invention, energy level and T₁ valuebetween the respective layers of the organic material layer, inherentmaterial properties (mobility, interfacial properties, etc.) and thelike can be optimized by forming a hole transport layer and/or anemission-auxiliary layer with the compound represented by the Formula 1,and thus it is possible to simultaneously improve the life span andefficiency of the organic electric element.

The organic electric element according to an embodiment of the presentinvention may be manufactured using various deposition methods. Theorganic electric element according to an embodiment of the presentinvention may be manufactured using a PVD (physical vapor deposition)method or CVD (chemical vapor deposition) method. For example, theorganic electric element may be manufactured by depositing a metal, aconductive metal oxide, or a mixture thereof on the substrate to formthe anode 120, forming the organic material layer including the holeinjection layer 130, the hole transport layer 140, the light emittinglayer 150, the electron transport layer 160, and the electron injectionlayer 170 thereon, and then depositing a material, which can be used asthe cathode 180, thereon.

Also, an emitting auxiliary layer 151 may be formed between a holetransport layer 140 and a light emitting layer 150, and an electrontransport auxiliary layer may be formed between a light emitting layer150 and an electron transport layer 160.

Also, the organic material layer may be manufactured in such a mannerthat a smaller number of layers are formed using various polymermaterials by a soluble process or solvent process, for example, spincoating, nozzle printing, inkjet printing, slot coating, dip coating,roll-to-roll, doctor blading, screen printing, or thermal transfer,instead of deposition. Since the organic material layer according to thepresent invention may be formed in various ways, the scope of protectionof the present invention is not limited by a method of forming theorganic material layer.

The organic electric element according to an embodiment of the presentinvention may be of a top emission type, a bottom emission type, or adual emission type depending on the material used.

WOLED (White Organic Light Emitting Device) has advantages of highresolution realization, an excellent processability, and being producedby using conventional color filter technologies for LCDs. Variousstructures for WOLED which mainly used as back light units have beensuggested and patented. WOLED may employ various arrangement methods,representatively, a parallel side-by-side arrangement method of R (Red),G (Green), B (Blue) light-emitting units, a vertical stack arrangementmethod of RGB light-emitting units, and a CCM (color conversionmaterial) method in which electroluminescence from a blue (B) organiclight emitting layer, and the present invention may be applied to suchWOLED.

Also, the organic electric element according to an embodiment of thepresent invention may be any one of an organic light emitting diode, anorganic solar cell, an organic photo conductor, an organic transistor,and an element for monochromatic or white illumination.

Another embodiment of the present invention provides an electronicdevice including a display device which includes the above describedorganic electric element, and a control unit for controlling the displaydevice. Here, the electronic device may be a wired/wirelesscommunication terminal which is currently used or will be used in thefuture, and covers all kinds of electronic devices including a mobilecommunication terminal such as a cellular phone, a personal digitalassistant (PDA), an electronic dictionary, a point-to-multipoint (PMP),a remote controller, a navigation unit, a game player, various kinds ofTVs, and various kinds of computers.

Hereinafter, the compound according to an aspect of the presentinvention will be described.

The compound according to an aspect of the present invention isrepresented by formula 1 below.

In the formula 1, each of symbols may be defined as follows.

Ar¹ to Ar⁴ are each independently selected from the group consisting ofa C₆-C₆₀ aryl group, a C₂-C₆₀ heterocyclic group containing at least oneheteroatom selected from the group consisting of O, N, S, Si, and P, afluorenyl group, a fused ring group of a C₃-C₆₀ aliphatic ring and aC₆-C₆₀ aromatic ring, a C₁-C₅₀ alkyl group, a C₂-C₂₀ alkenyl group, aC₂-C₂₀ alkynyl group, a C₁-C₃₀ alkoxyl group and a C₆-C₃₀ aryloxy group,with the proviso that a triphenylene group is excluded from Ar² and acarbazole group is excluded from Ar³ and Ar⁴.

Preferably, at least one of Ar¹ to Ar⁴ is represented by the followingFormula 5:

In the formula 5, each of symbols may be defined as follows, and “*”indicates the bonding position.

Y is S, O or C(R^(d))(R^(e)), wherein R^(d) and R^(e) are eachindependently selected from the group consisting of a C₆-C₂₀ aryl group,a fluorenyl group, a C₂-C₂₀ heterocyclic group containing at least oneheteroatom selected from the group consisting of O, N, S, Si, and P, afused ring group of a C₃-C₂₀ aliphatic ring and a C₆-C₂₀ aromatic ring,a C₁-C₂₀ alkyl group, a C₂-C₂₀ alkenyl group, a C₂-C₂₀ alkynyl group, aC₁-C₃₀ alkoxyl group and a C₆-C₃₀ aryloxy group.

R⁶ and R⁷ are each independently selected from the group consisting of aC₆-C₂₀ aryl group, a fluorenyl group, a C₂-C₂₀ heterocyclic groupcontaining at least one heteroatom selected from the group consisting ofO, N, S, Si, and P, a fused ring group of a C₃-C₂₀ aliphatic ring and aC₆-C₂₀ aromatic ring, a C₁-C₂₀ alkyl group, a C₂-C₂₀ alkenyl group, aC₂-C₂₀ alkynyl group, a C₁-C₃₀ alkoxyl group and a C₆-C₃₀ aryloxy group,h is an integer of 0 to 4, g is an integer of 0 to 3, and plural R⁶s andplural R⁷s are each the same or different from each other where h and gare each an integer of 2 or more.

In addition, when at least one of Ar¹ to Ar⁴ in Formula 1 is the Formula5, preferably, the Formula 5 is one of the following Formulas 1-1 to1-3, more preferably, Y in the formula 5 is S.

In the above Formulas 1-1 to 1-3, the symbols such as Ar¹ to Ar⁴, R¹ toR³, R⁶, R⁷, L¹, m, n, o, g, h and the like are the same as defined inFormula 1.

Where Ar¹ is an aryl group, Ar¹ may be preferably a C₆-C₃₀ aryl group,more preferably a C₆-C₁₈ aryl group, for example, phenyl, naphthyl,biphenyl, terphenyl, phenanthryl, triphenylene or the like; when Ar¹ isa heterocyclic group, Ar¹ may be preferably a C₂-C₃₀ heterocyclic group,more preferably a C₂-C₁₂ heterocyclic group, for example,dibenzothiophene, carbazole, dibenzofuran or the like; when Ar¹ is afluorenyl group, Ar¹ may be, for example, 9,9-dimethyl-9H-fluorene.

When Ar² is an aryl group, Ar² may be preferably a C₆-C₃₀ aryl group,more preferably a C₆-C₁₄ aryl group, for example, phenyl, naphthyl,biphenyl, phenanthryl or the like, but triphenylene is excluded from thearyl group; when Ar² is a heterocyclic group, Ar² may be preferably aC₂-C₃₀ heterocyclic group, more preferably a C₂-C₁₆ heterocyclic group,for example, dibenzothiophene, benzonaphthothiophene, dibenzofuran,isoquinoline or the like; when Ar² is a fluorenyl group, Ar² may be9,9-dimethyl-9H-fluorene.

When Ar³ and Ar⁴ are each an aryl group, Ar³ and Ar⁴ may be preferably aC₆-C₃₀ aryl group, more preferably a C₆-C₁₈ aryl group, for example,phenyl, naphthyl, biphenyl, terphenyl, phenanthryl or the like; when Ar³and Ar⁴ are each a heterocyclic group, Ar³ and Ar⁴ may be preferably aC₂-C₃₀ heterocyclic group, more preferably a C₂-C₁₆ heterocyclic group,for example, pyridine, dibenzothiophene, benzonaphthothiophene,dibenzofuran, phenanthroline, isoquinoline or the like, but carbazole isexcluded from the heterocyclic group; when Ar³ and Ar⁴ are each afluorenyl group, Ar³ and Ar⁴ may be, for example,9,9-dimethyl-9H-fluorene, 9,9-diphenyl-9H-fluorene, 9,9′-spirofluoreneor the like.

R¹ to R³ are each independently selected from the group consisting ofdeuterium, tritium, halogen, a cyano group, a nitro group, a C₆-C₆₀ arylgroup, a fluorenyl group, a C₂-C₆₀ heterocyclic group containing atleast one heteroatom selected from the group consisting of O, N, S, Si,and P, a fused ring group of a C₃-C₆₀ aliphatic ring and a C₆-C₆₀aromatic ring, a C₁-C₅₀ alkyl group, a C₂-C₂₀ alkenyl group, a C₂-C₂₀alkynyl group, a C₁-C₃₀ alkoxyl group and a C₆-C₃₀ aryloxy group.

m and o are each an integer of 0 to 4, n is an integer of 0 to 3, andplural R¹s to plural R³s are each the same or different from each otherwhere m, n or o is each an integer of 2 or more. When R¹ to R³ are eachan aryl group, R¹ to R³ may be preferably a C₆-C₃₀ aryl group, morepreferably a C₆-C₁₀ aryl group, for example, phenyl, naphthyl or thelike.

Further, adjacent R¹ groups, adjacent R² groups and/or adjacent R³groups may optionally be linked together to each other to form a ring,where m, n or o is each an integer of 2 or more. Here, the ring may be amonocyclic or polycyclic ring, and the ring may be a C₆-C₃₀ aryl group,a fluorenyl group, a C₂-C₆₀ heterocyclic group containing at least oneheteroatom selected from the group consisting of O, N, S, Si, and P, afused ring group of a C₃-C₆₀ aliphatic ring and a C₆-C₆₀ aromatic ringor the like. When adjacent R¹ groups, adjacent R² groups and/or adjacentR³ groups are linked together to each other to form an aryl group, thering may be, for example, a benzene ring, as a result, naphthalene,phenanthrene or the like may be formed together with the benzene ring towhich they are bonded.

L¹ is selected from the group consisting of a C₆-C₆₀ arylene group, afluorenylene group, a C₂-C₆₀ heterocyclic group containing at least oneheteroatom selected from the group consisting of O, N, S, Si, and P, afused ring group of a C₃-C₆₀ aliphatic ring and a C₆-C₆₀ aromatic ring,and an aliphatic hydrocarbon group.

When L¹ is an arylene group, L¹ may be preferably a C₆-C₃₀ arylenegroup, more preferably a C₆-C₁ arylene group, for example, phenylene,biphenyl, terphenyl, naphthalene, anthrancene, phenanthrene or the like;when L¹ is a heterocyclic group, L¹ may be preferably a C₂-C₃₀heterocyclic group, more preferably a C₂-C₁₈ heterocyclic group, forexample, dibenzofuran, dibenzothiophene, benzonaphthothiophene or thelike; when L¹ is a fluorenyl group, L¹ may be, for example,9,9-dimethyl-9H-fluorene.

The aryl group, arylene group, fluorenyl group, fluorenylene group,heterocyclic group, fused ring group, alkyl group, alkenyl group,alkynyl group, alkoxyl group and aryloxyl group of Ar¹ to Ar⁴, R¹ to R³,R⁶, R⁷ and L¹ are each optionally further substituted with one or moresubstituents selected from the group consisting of deuterium, halogen, asilane group substituted or unsubstituted with C₁-C₂₀ alkyl group orC₆-C₂₀ aryl group, a siloxane group, a boron group, a germanium group, acyano group, a nitro group, a C₁-C₂₀ alkylthio group, a C₁-C₂₀ alkoxylgroup, a C₁-C₂₀ alkyl group, a C₂-C₂₀ alkenyl group, a C₂-C₂₀ alkynylgroup, a C₆-C₂₀ aryl group, a C₆-C₂₀ aryl group substituted withdeuterium, a fluorenyl group, a C₂-C₂₀ heterocyclic group containing atleast one heteroatom selected from the group consisting of O, N, S, Si,and P, a C₃-C₂₀ cycloalkyl group, a C₇-C₂₀ arylalkyl group and a C₈-C₂₀arylalkenyl group, wherein adjacent substituents may optionally belinked together to form a ring where the substituents are adjacent, withthe proviso that where Ar² to Ar⁴ is the aryl group, the aryl group canbe substituted with the heterocyclic group wherein the heterocyclicgroup excludes a carbazole group, a dibenzothienyl group and adibenzofuryl group.

Preferably, the Formula 1 is represented by one of the followingFormulas 2 to 4:

wherein each of symbols is the same as defined in the Formula 1. Thatis, Ar¹ to Ar⁴, R¹ to R³, L¹, m, n and o are the same as defined in theFormula 1.

Preferably, L¹ is represented by one of the following Formulas L1-1 toL1-7 in Formulas 1 to 4:

In the formulas L1-1 to L1-7, each of symbols may be defined as follows,and “*” indicates the bonding position.

X is S, O, C(R^(a))(R^(b)) or N(R^(c)). Here, R^(a), R^(b) and R^(c) areeach independently selected from the group consisting of a C₆-C₂₀ arylgroup, a fluorenyl group, a C₂-C₂₀ heterocyclic group containing atleast one heteroatom selected from the group consisting of O, N, S, Si,and P, a fused ring group of a C₃-C₂₀ aliphatic ring and a C₆-C₆₀aromatic ring, a C₁-C₂₀ alkyl group, a C₂-C₂₀ alkenyl group, a C₂-C₂₀alkynyl group, a C₁-C₃₀ alkoxyl group and a C₆-C₃₀ aryloxy group, andR^(a) and R^(b) may optionally be linked together to form a spirocompound together with a carbon to which they are bonded. Where R^(a)and R^(b) are each alkyl group, R^(a) and R^(b) may be preferably aC₁-C₁₀ alkyl group, for example, methyl group.

R⁴ and R⁵ are each independently selected from the group consisting of aC₆-C₂₀ aryl group, a fluorenyl group, a C₂-C₂₀ heterocyclic groupcontaining at least one heteroatom selected from the group consisting ofO, N, S, Si, and P, a fused ring group of a C₃-C₂₀ aliphatic ring and aC₆-C₆₀ aromatic ring, a C₁-C₂₀ alkyl group, a C₂-C₂₀ alkenyl group, aC₂-C₂₀ alkynyl group, a C₁-C₃₀ alkoxyl group and a C₆-C₃₀ aryloxy group.a and b are each an integer of 0 to 4, c is an integer of 0 to 6, d isan integer of 0 to 5, e and f are each an integer of 0 to 3, and each ofthe plurality of R⁴s and each of the plurality of R⁵s are the same ordifferent from each other where a, b, c, d, e and f are each an integerof 2 or more.

Preferably, the Formula L1-1 is one of the following structures.

Specifically, the compound represented by formula 1 may be any one ofthe following compounds.

In another aspect of the present invention, the present inventionprovides an organic electric element comprising a first electrode, asecond electrode, and an organic material layer formed between the firstelectrode and the second electrode, wherein the organic material layercomprises the compound represented by the formula 1.

The organic material layer comprises at least one of a hole injectionlayer, one or more hole transport layers, an emission-auxiliary layer, alight emitting layer, an electron transport auxiliary layer, one or moreelectron transport layers and an electron injection layer. At least onelayer of the above layers may comprise the compound represented by theformulas 1 to 4 as a single compound or as a mixture of two or morekinds. Preferably, the compound represented by the formulas 1 to 4 maybe material of one or more hole transport layers or/and theemission-auxiliary layer.

In addition, the present invention, the present invention provides anorganic electric element further comprising a layer for improvingluminous efficiency formed on at least one side of sides of the firstelectrode and the second electrode, wherein at least one side is notfacing the organic material layer, and the organic material layer may beformed by any one of the processes of spin coating, nozzle printing,inkjet printing, slot coating, dip coating or roll-to-roll.

Hereinafter, synthesis example of the compound represented by Formula 1,wherein the compound is used as material of the organic material layer,and preparation method of an organic electric element according to oneembodiment of the present invention will be described in detail by wayof examples. However, the present invention is not limited to thefollowing examples.

SYNTHESIS EXAMPLE

As shown in Reaction Scheme 1 below, the compounds (final products)represented by Formula 1 according to the present invention can besynthesized by reacting Sub 1 with Sub 2, but there is no limitationthereto. The symbols of Ar¹ to Ar⁴, R¹ to R³, L¹, m, n and o and thelike are the same as defined in Formula 1.

I. Synthesis of Sub 1

Sub 1 of the Reaction Scheme 1 can be synthesized according to thereaction routes of the following Reaction Schemes 2 and 3, but it is notlimited thereto.

The synthesis method disclosed in Korean Patent No. 10-1535606(registered on Jul. 23, 2015) owned by the applicant of the presentinvention was used for the synthesis of Sub 1-II (Reaction Scheme 3).

Synthesis examples of the compounds belonging to Sub 1 are as follows.

1. Synthesis Example of Sub 1-1

After Sub 1-II-1 (CAS Registry Number: 1246669-45-3) (64.3 g, 174.13mmol) was dissolved in THE (640 ml) in a round bottom flask,1-bromo-4-chlorobenzene (CAS Registry Number: 106-39-8) (40 g, 208.95mmol), Pd(PPh₃)₄ (6 g, 5.22 mmol), NaOH (20.9 g, 522.38 mmol), water(320 ml) were added to the solution, and then the mixture was stirred at80° C. When the reaction was completed, the reaction product wasextracted with CH₂Cl₂ and water, and then the organic layer was driedwith MgSO₄ and concentrated. Then, the concentrate was applied to silicagel column and recrystallized to obtain 49.9 g (yield: 81%) of theproduct.

2. Synthesis Example of Sub 1-4

1-bromo-3-chlorobenzene (CAS Registry Number: 108-37-2) (42.6 g, 222.60mmol), Pd(PPh₃)₄ (6.4 g, 5.57 mmol), NaOH (22.3 g, 556.50 mmol), THE(680 ml), and water (340 ml) were added to Sub 1-II-1 (CAS RegistryNumber: 1246669-45-3) (68.5 g, 185.50 mmol), and then the same method asin synthesis of Sub 1-1 were proceeded to obtain 54.5 g (yield: 83%) ofthe product.

3. Synthesis Example of Sub 1-9

(1) Synthesis of Sub 1-I-9

After 2-bromo-9H-carbazole (CAS Registry Number: 3652-90-2) (50.1 g,203.57 mmol) was dissolved in nitrobenzene (1020 ml) in a round bottomflask, 4-(3-iodophenyl)pyridine (CAS Registry Number: 1261579-06-9)(114.5 g, 407.14 mmol), Na₂SO₄ (28.9 g, 203.57 mmol), K₂CO₃ (28.1 g,203.57 mmol), Cu (3.9 g, 61.1 mmol) were added to the solution and themixture was stirred at 200° C. When the reaction was completed,nitrobenzene was removed by distillation and the resultant was extractedwith CH₂Cl₂ and water. Then, the organic layer was dried with MgSO₄ andconcentrated. The concentrate was applied to silica gel column andrecrystallized to obtain 50.4 g (yield: 62%) of the product.

(2) Synthesis of Sub 1-II-9

After Sub 1-I-9 (50.4 g, 126.22 mmol) obtained in the above synthesiswas dissolved in DMF (630 ml) in a round bottom flask,bis(pinacolato)diboron (35.3 g, 138.85 mmol), Pd(dppf)Cl₂ (3.1 g, 3.79mmol), KOAc (37.2 g, 378.67 mmol) were added to the solution and themixture was stirred at 90° C. When the reaction was completed, DMF wasremoved by distillation and the resultant was extracted with ether andwater. Then the organic layer was dried with MgSO₄ and concentrated. Theconcentrate was applied to silica gel column and recrystallized toobtain 42.8 g (yield: 76%) of the product.

(3) Synthesis of Sub 1-9

After 1-bromo-2-chlorobenzene (CAS Registry Number: 694-80-4) (18.4 g,95.89 mmol), Pd(PPh₃)₄ (3.3 g, 2.88 mmol), NaOH (11.5 g, 287.66 mmol),THE (320 ml), water (160 ml) were added to Sub 1-II-9 (42.8 g, 95.89mmol) obtained in the above synthesis, 34.3 g (yield: 83%) of theproduct was obtained by proceeding with the same method as in synthesisof Sub 1-1.

4. Synthesis Example of Sub 1-16

After 1-bromo-3-chlorobenzene (CAS Registry Number: 108-37-2) (8.1 g,42.35 mmol), Pd(PPh₃)₄ (1.2 g, 1.06 mmol), NaOH (4.2 g, 105.88 mmol),THE (130 ml), water (65 ml) were added to Sub 1-II-16 (CAS RegistryNumber: 1646271-66-0) (14.8 g, 35.29 mmol), 11 g (yield: 77%) of theproduct was obtained by proceeding with the same method as in synthesisof Sub 1-1.

5. Synthesis Example of Sub 1-29

(1) Synthesis of Sub 1-I-29

After 2-iododibenzo[b,d]thiophene (CAS Registry Number: 177586-41-3)(45.4 g, 146.28 mmol), Na₂SO₄ (10.4 g, 73.14 mmol), K₂CO₃ (10.1 g, 73.14mmol), Cu (1.4 g, 21.94 mmol), nitrobenzene (365 ml) were added to2-bromo-9H-carbazole (CAS Registry Number: 3652-90-2) (18 g, 73.14mmol), 18.8 g (yield: 60%) of the product was obtained by proceedingwith the same method as in synthesis of Sub 1-I-9.

(2) Synthesis of Sub 1-II-29

After bis(pinacolato)diboron (12.3 g, 48.28 mmol), Pd(dppf)Cl₂ (1.1 g,1.32 mmol), KOAc (12.9 g, 131.67 mmol), DMF (220 ml) were added to Sub1-I-9 (18.8 g, 43.89 mmol) obtained in the above synthesis, 16.9 g(yield: 81%) of the product was obtained by proceeding with the samemethod as in synthesis of Sub 1-11-9.

(3) Synthesis of Sub 1-29

After 1-bromo-3-chlorobenzene (CAS Registry Number: 108-37-2) (6.81 g,35.55 mmol), Pd(PPh₃)₄ (1.2 g, 1.07 mmol), NaOH (4.3 g, 106.64 mmol),THE (120 ml), water (60 ml) were added to Sub 1-II-29 (16.9 g, 35.55mmol) obtained in the above synthesis, 14.2 g (yield: 87%) of theproduct was obtained by proceeding with the same method as in synthesisof Sub 1-1.

The compounds belonging to Sub 1 may be, but not limited to, thefollowing compounds, and Table 1 shows FD-MS (Field Desorption-MassSpectrometry) values of them.

TABLE 1 Compound FD-MS Compound FD-MS Sub 1-1 m/z = 353.10(C₂₄H₁₆ClN =353.85) Sub 1-2 m/z = 403.11(C₂₈H₁₈ClN = 403.91) Sub 1-3 m/z =403.11(C₂₈H₁₈ClN = 403.91) Sub 1-4 m/z = 353.10(C₂₄H₁₆ClN = 353.85) Sub1-5 m/z = 429.13(C₃₀H₂₀ClN = 429.95) Sub 1-6 m/z = 505.16(C₃₆H₂₄ClN =506.05) Sub 1-7 m/z = 429.13(C₃₀H₂₀ClN = 429.95) Sub 1-8 m/z =353.10(C₂₄H₁₆ClN = 353.85) Sub 1-9 m/z = 430.12(C₂₉H₁₉ClN₂ = 430.94) Sub1-10 m/z = 459.08(C₃₀H₁₈ClNS = 459.99) Sub 1-11 m/z = 429.13(C₃₀H₂₀ClN =429.95) Sub 1-12 m/z = 358.13(C₂₄H₁₁D₅ClN = 358.88) Sub 1-13 m/z =469.16(C₃₃H₂₄ClN = 470.01) Sub 1-14 m/z = 459.08(C₃₀H₁₈ClNS = 459.99)Sub 1-15 m/z = 429.13(C₃₀H₂₀ClN = 429.95) Sub 1-16 m/z = 403.11(C₂₈H₁₈ClN = 403.91) Sub 1-17 m/z = 403.11(C₂₈H₁₈ClN = 403.91) Sub 1-18 m/z =503.14(C₃₆H₂₂ClN = 504.03) Sub 1-19 m/z = 453.13(C₃₂H₂₀ClN = 453.97) Sub1-20 m/z = 453.13(C₃₂H₂₀ClN = 453.97) Sub 1-21 m/z = 429.13(C₃₀H₂₀ClN =429.95) Sub 1-22 m/z = 429.13(C₃₀H₂₀ClN = 429.95) Sub 1-23 m/z =493.16(C₃₅H₂₄ClN = 494.03) Sub 1-24 m/z = 371.09(C₂₄H₁₅ClFN = 371.84)Sub 1-25 m/z = 480.14(C₃₃H₂₁ClN₂ = 481.00) Sub 1-26 m/z =518.15(C₃₆H₂₃ClN₂ = 519.04) Sub 1-27 m/z = 403.11(C₂₈H₁₈ClN = 403.91)Sub 1-28 m/z = 378.09(C₂₅H₁₅ClN₂ = 378.86) Sub 1-29 m/z =459.08(C₃₀H₁₈ClNS = 459.99) Sub 1-30 m/z = 429.13(C₃₀H₂₀ClN = 429.95)Sub 1-31 m/z = 503.14(C₃₆H₂₂ClN = 504.03) Sub 1-32 m/z =453.13(C₃₂H₂₀ClN = 453.97) Sub 1-33 m/z = 443.11(C₃₀H₁₈ClNO = 443.93)

II. Synthesis of Sub 2

Sub 2 of the Reaction Scheme 1 can be synthesized according to thereaction route of the following Reaction Scheme 9, but there is nolimitation thereto.

In the above Reaction Scheme 9, the synthetic method disclosed in KoreanPatent No. 10-1251451 (registered on Mar. 31, 2013) owned by theapplicant of the present invention was used for the synthesis of theamine (HN—Ar³Ar⁴) reactant.

Synthesis examples of the compounds belonging to Sub 2 are as follows.

1. Synthesis Example of Sub 2-7

(1) Synthesis of Sub 2-I-7

After N-phenyl-[1,1′-biphenyl]-4-amine (CAS Registry Number: 32228-99-2)(13.1 g, 53.40 mmol) was dissolved in toluene (445 ml) in a round bottomflask, 1-bromo-4-iodobenzene (CAS Registry Number: 589-87-7) (22.7 g,80.10 mmol), Pd₂(dba)₃ (1.5 g, 1.60 mmol), 50% P(t-Bu)₃ (2.1 ml, 4.27mmol), NaOt-Bu (15.4 g, 160.19 mmol) were added to the solution and themixture was stirred at 70° C. When the reaction was completed, thereaction product was extracted with CH₂Cl₂ and water, and then theorganic layer was dried with MgSO₄ and concentrated. Then, theconcentrate was applied to silica gel column and recrystallized toobtain 15.6 g (yield: 73%) of the product.

(2) Synthesis of Sub 2-7

After Sub 2-I-7 (15.6 g, 38.97 mmol) was dissolved in toluene (325 ml)in a round bottom flask, naphthalen-1-amine (CAS Registry Number:134-32-7) (8.4 g, 58.45 mmol), Pd₂(dba)₃ (1.1 g, 1.17 mmol), 50%P(t-Bu)₃ (1.5 ml, 3.12 mmol), NaOt-Bu (11.2 g, 116.91 mmol) were addedthe solution and the mixture was stirred at 100° C. When the reactionwas completed, the reaction product was extracted with CH₂Cl₂ and water,and then the organic layer was dried with MgSO₄ and concentrated. Then,the concentrate was applied to silica gel column and recrystallized toobtain 14.1 g (yield: 78%) of the product.

2. Synthesis Example of Sub 2-11

(1) Synthesis of Sub 2-I-11

After 1-bromo-3-iodobenzene (CAS Registry Number: 591-18-4) (45.29 g,160.07 mmol), Pd₂(dba)₃ (2.9 g, 3.2 mmol), 50% P(t-Bu)₃ (4.2 ml, 8.54mmol), NaOt-Bu (30.8 g, 320.14 mmol), toluene (890 ml) were added todi([1,1′-biphenyl]-4-yl)amine (CAS Registry Number: 102113-98-4) (34.3g, 106.71 mmol), 36.1 g (yield: 71%) of the product was obtained byproceeding with the same method as in synthesis of Sub 2-I-7.

(2) Synthesis of Sub 2-11

After aniline (CAS Registry Number: 62-53-3) (10.6 g, 113.66 mmol),Pd₂(dba)₃ (2.1 g, 2.27 mmol), 50% P(t-Bu)₃ (3 ml, 6.06 mmol), NaOt-Bu(21.9 g, 227.32 mmol), toluene (630 ml) were added to Sub 2-I-11 (36.1g, 75.77 mmol) obtained in the above synthesis, 29.6 g (yield: 80%) ofthe product was obtained by proceeding with the same method as insynthesis of Sub 2-I-7.

3. Synthesis Example of Sub 2-14

(2) Synthesis of Sub 2-I-14

After 1-bromo-3-iodobenzene (CAS Registry Number: 591-18-4) (21.6 g,76.43 mmol), Pd₂(dba)₃ (1.4 g, 1.53 mmol), 50% P(t-Bu) ((2 ml, 4.08mmol), NaOt-Bu (14.7 g, 152.86 mmol), toluene (425 ml) were added toN-phenyl-[1,1-biphenyl]-4-amine (CAS Registry Number: 32228-99-2) (12.5g, 50.95 mmol), 15.3 g (yield: 75%) of the product was obtained byproceeding with the same method as in synthesis of Sub 2-I-7.

(2) Synthesis of Sub 2-14

After benzen-d₅-amine (CAS Registry Number: 4165-61-1) (5.6 g, 57.33mmol), Pd₂(dba)₃ (1.1 g, 1.15 mmol), 50% P(t-Bu)₃ (1.5 ml, 3.06 mmol),NaOt-Bu (11.02 g, 114.66 mmol), toluene (320 ml) were added to Sub2-I-14 (15.3 g, 38.22 mmol) obtained in the above synthesis, 12.3 g(yield: 77%) of the product was obtained by proceeding with the samemethod as in synthesis of Sub 2-I-7.

4. Synthesis Example of Sub 2-40

(1) Synthesis of Sub 2-I-40

After 1-bromo-3-iodobenzene (CAS Registry Number: 591-18-4) (27.8 g,98.18 mmol), Pd₂(dba)₃ (1.8 g, 1.96 mmol), 50% P(t-Bu)₃ (2.6 ml, 5.24mmol), NaOt-Bu (18.87 g, 196.36 mmol), toluene (545 ml) were added toN-(naphthalen-1-yl)dibenzo[b,d]thiophen-4-amine (CAS Registry Number:1464825-38-4) (21.3 g, 65.45 mmol), 21.7 g (yield: 69%) of the productwas obtained by proceeding with the same method as in synthesis of Sub2-I-7.

(2) Synthesis of Sub 2-40

After aniline (CAS Registry Number: 62-53-3) (6.31 g, 67.75 mmol),Pd₂(dba)₃ (1.24 g, 1.36 mmol), 50% P(t-Bu)₃ (1.8 ml, 3.61 mmol), NaOt-Bu(13 g, 135.51 mmol), toluene (375 ml) were added to Sub 2-I-40 (21.7 g,45.17 mmol) obtained in the above synthesis, 18 g (yield: 81%) of theproduct was obtained by proceeding with the same method as in synthesisof Sub 2-I-7.

5. Synthesis Example of Sub 2-45

(1) Synthesis of Sub 2-I-45

After 1-bromo-3-iodobenzene (CAS Registry Number: 591-18-4) (45.6 g,161.32 mmol), Pd₂(dba)₃ (3 g, 3.23 mmol), 50% P(t-Bu)₃ (4.2 ml, 8.60mmol), NaOt-Bu (31 g, 322.64 mmol), toluene (895 ml) were added todiphenylamine (CAS Registry Number: 122-39-4) (18.2 g, 107.55 mmol),23.7 g (yield: 68%) of the product was obtained by proceeding with thesame method as in synthesis of Sub 2-I-7.

(2) Synthesis of Sub 2-45

After dibenzo[b,d]thiophen-2-amine (CAS Registry Number: 7428-91-3)(21.9 g, 109.65 mmol), Pd₂(dba)₃ (2 g, 2.19 mmol), 50% P(t-Bu)₃ (2.9 ml,5.85 mmol), NaOt-Bu (21.1 g, 219.3 mmol), toluene (610 ml) were added toSub 2-I-45 (23.7 g, 73.1 mmol) obtained in the above synthesis, 25.6 g(yield: 79%) of the product was obtained by proceeding with the samemethod as in synthesis of Sub 2-I-7.

6. Synthesis Example of Sub 2-58

(1) Synthesis of Sub 2-I-58

After 2-bromo-7-iododibenzo[b,d]thiophene (CAS Registry Number:1910080-84-0) (34.5 g, 88.64 mmol), Pd₂(dba)₃ (1.6 g, 1.77 mmol), 50%P(t-Bu)₃ (2.3 ml, 4.73 mmol), NaOt-Bu (17 g, 177.27 mmol), toluene (490ml) were added to diphenylamine (CAS Registry Number: 122-39-4) (10 g,59.09 mmol), 21.1 g (yield: 83%) of the product was obtained byproceeding with the same method as in synthesis of Sub 2-1-7.

(2) Synthesis of Sub 2-58

After aniline (CAS Registry Number: 62-53-3) (6.9 g, 73.54 mmol),Pd₂(dba)₃ (1.4 g, 1.47 mmol), 50% P(t-Bu)₃ (1.9 ml, 3.92 mmol), NaOt-Bu(14.1 g, 147.09 mmol), toluene (410 ml) were added to Sub 2-I-58 (21.1g, 49.03 mmol) obtained in the above synthesis, 18.4 g (yield: 85%) ofthe product was obtained by proceeding with the same method as insynthesis of Sub 2-I-7.

7. Synthesis Example of Sub 2-66

(1) Synthesis of Sub 2-I-66

After 3-bromo-5-iodo-1,1′-biphenyl (CAS Registry Number: 136649-44-0)(35 g, 97.50 mmol), Pd₂(dba)₃ (1.8 g, 1.95 mmol), 50% P(t-Bu)₃ (2.5 ml,5.2 mmol), NaOt-Bu (18.7 g, 195.00 mmol), toluene (540 ml) were added todiphenylamine (CAS Registry Number: 122-39-4) (11 g, 65.00 mmol), 18.7 g(yield: 72%) of the product was obtained by proceeding with the samemethod as in synthesis of Sub 2-I-7.

(2) Synthesis of Sub 2-66

After dibenzo[b,d]thiophen-2-amine (CAS Registry Number: 7428-91-3) (14g, 70.07 mmol), Pd₂(dba)₃ (1.3 g, 1.40 mmol), 50% P(t-Bu)₃ (1.8 ml, 3.74mmol), NaOt-Bu (13.5 g, 140.14 mmol), toluene (390 ml) were added to Sub2-I-66 (18.7 g, 46.71 mmol) obtained in the above synthesis, 18.4 g(yield: 76%) of the product was obtained by proceeding with the samemethod as in synthesis of Sub 2-I-7.

8. Synthesis Example of Sub 2-89

(1) Synthesis of Sub 2-I-89

After 1-bromo-3-iodo-5-methylbenzene (CAS Registry Number: 116632-38-3)(25.3 g, 85.09 mmol), Pd₂(dba)₃ (1.6 g, 1.70 mmol), 50% P(t-Bu)₃ (2.2ml, 4.54 mmol), NaOt-Bu (16.4 g, 170.18 mmol), toluene (470 ml) wereadded to diphenylamine (CAS Registry Number: 122-39-4) (9.6 g, 56.73mmol), 13.4 g (yield: 70%) of the product was obtained by proceedingwith the same method as in synthesis of Sub 2-I-7.

(2) Synthesis of Sub 2-89

After dibenzo[b,d]thiophen-2-amine (CAS Registry Number: 7428-91-3)(11.8 g, 59.42 mmol), Pd₂(dba)₃ (1.1 g, 1.19 mmol), 50% P(t-Bu)₃ (1.5ml, 3.17 mmol), NaOt-Bu (11.4 g, 118.85 mmol), toluene (330 ml) wereadded to Sub 2-I-89 (13.4 g, 39.62 mmol) obtained in the abovesynthesis, 12.8 g (yield: 71%) of the product was obtained by proceedingwith the same method as in synthesis of Sub 2-I-7.

The compounds belonging to Sub 2 may be, but not limited to, thefollowing compounds, and Table 2 shows FD-MS (Field Desorption-MassSpectrometry) values of them.

TABLE 2 Compound FD-MS Compound FD-MS Sub 2-1 m/z = 336.16(C₂₄H₂₀N₂ =336.44) Sub 2-2 m/z = 412.19(C₃₀H₂₄N₂ = 412.54) Sub 2-3 m/z =488.23(C₃₆H₂₈N₂ = 488.63) Sub 2-4 m/z = 336.16(C₂₄H₂₀N₂ = 336.44) Sub2-5 m/z = 413.19(C₃₉H₂₃N₃ = 413.52) Sub 2-6 m/z = 442.15(C₃₀H₂₂N₂S =442.58) Sub 2-7 m/z = 462.21(C₃₄H₂₆N₂ = 462.60) Sub 2-8 m/z =488.23(C₃₆H₂₈N₂ = 488.63) Sub 2-9 m/z = 488.23(C₃₆H₂₈N₂ = 488.63) Sub2-10 m/z = 412.19(C₃₀H₂₄N₂ = 412.54) Sub 2-11 m/z = 488.23(C₃₆H₂₈N₂ =488.63) Sub 2-12 m/z = 488.23(C₃₆H₂₈N₂ = 488.63) Sub 2-13 m/z =488.23(C₃₆H₂₈N₂ = 488.63) Sub 2-14 m/z = 417.23(C₃₀H₁₉D₅N₂ = 417.57) Sub2-15 m/z = 462.21(C₃₄H₂₆N₂ = 462.60) Sub 2-16 m/z = 462.21(C₃₄H₂₆N₂ =462.60) Sub 2-17 m/z = 412.19(C₃₀H₂₄N₂ = 412.54) Sub 2-18 m/z =564.26(C₄₂H₃₂N₂ = 564.73) Sub 2-19 m/z = 436.19(C₃₂H₂₄N₂ = 436.56) Sub2-20 m/z = 436.19(C₃₂H₂₄N₂ = 436.56) Sub 2-21 m/z = 412.19(C₃₀H₂₄N₂ =412.54) Sub 2-22 m/z = 539.24(C₃₉H₂₉N₃ = 539.68) Sub 2-23 m/z =463.20(C₃₃H₂₅N₃ = 463.58) Sub 2-24 m/z = 564.26(C₄₂H₃₂N₂ = 564.73) Sub2-25 m/z = 336.16(C₂₄H₂₀N₂ = 336.44) Sub 2-26 m/z = 412.19(C₃₀H₂₄N₂ =412.54) Sub 2-27 m/z = 436.19(C₃₂H₂₄N₂ = 436.56) Sub 2-28 m/z =436.19(C₃₂H₂₄N₂ = 436.56) Sub 2-29 m/z = 548.14(C₃₆H₂₄N₂S₂ = 548.72) Sub2-30 m/z = 532.16(C₃₆H₂₄N₂SO = 532.66) Sub 2-31 m/z = 452.23(C₃₃H₂₈N₂ =452.60) Sub 2-32 m/z = 516.18(C₃₆H₂₄N₂O₂ = 516.60) Sub 2-33 m/z =412.19(C₃₀H₂₄N₂ = 412.54) Sub 2-34 m/z = 592.20(C₄₂H₂₈N₂S = 592.76) Sub2-35 m/z = 442.15(C₃₀H₂₂N₂S = 442.58) Sub 2-36 m/z = 502.20(C₃₆H₂₆N₂O =502.62) Sub 2-37 m/z = 518.18(C₃₆H₂₆N₂S = 518.68) Sub 2-38 m/z =442.15(C₃₀H₂₂N₂S = 442.58) Sub 2-39 m/z = 442.15(C₃₀H₂₂N₂S = 442.58) Sub2-40 m/z = 492.17(C₃₄H₂₄N₂S = 492.64) Sub 2-41 m/z = 568.20(C₄₀H₂₈N₂ =568.74) Sub 2-42 m/z = 426.17(C₃₀H₂₂N₂O = 426.52) Sub 2-43 m/z =542.18(C₃₈H₂₆N₂S = 542.70) Sub 2-44 m/z = 618.21(C₄₄H₃₀N₂S = 618.80) Sub2-45 m/z = 442.15(C₃₀H₂₂N₂S = 442.58) Sub 2-46 m/z = 518.18(C₃₆H₂₆N₂S =518.68) Sub 2-47 m/z = 518.18(C₃₆H₂₆N₂S = 518.68) Sub 2-48 m/z =586.23(C₃₆H₃₈N₂SSi₂ = 586.94) Sub 2-49 m/z = 492.17(C₃₄H₂₄N₂S = 492.64)Sub 2-50 m/z = 518.18(C₃₆H₂₆N₂S = 518.68) Sub 2-51 m/z =516.18(C₃₆H₂₄N₂O₂ = 516.60) Sub 2-52 m/z = 426.17(C₃₀H₂₂N₂O = 426.52)Sub 2-53 m/z = 436.19(C₃₂H₂₄N₂ = 436.56) Sub 2-54 m/z = 542.24(C₃₉H₃₀N₂O= 542.68) Sub 2-55 m/z = 442.15(C₃₀H₂₂N₂S = 442.58) Sub 2-56 m/z =518.18(C₃₆H₂₆N₂S = 518.68) Sub 2-57 m/z = 518.18(C₃₆H₂₆N₂S = 518.68) Sub2-58 m/z = 442.15(C₃₀H₂₂N₂S = 442.58) Sub 2-59 m/z = 518.18(C₃₆H₂₆N₂S =518.68) Sub 2-60 m/z = 548.14(C₃₆H₂₄N₂S₂ = 548.72) Sub 2-61 m/z =442.15(C₃₀H₂₂N₂S = 442.58) Sub 2-62 m/z = 548.14(C₃₆H₂₄N₂S₂ = 548.72)Sub 2-63 m/z = 582.18(C₄₀H₂₆N₂OS = 582.72) Sub 2-64 m/z =528.26(C₃₉H₃₂N₂ = 528.70) Sub 2-65 m/z = 624.26(C₄ ₇H₃₂N₂ = 624.79) Sub2-66 m/z = 518.18(C₃₆H₂₆N₂S = 518.68) Sub 2-67 m/z = 518.18(C₃₆H₂₆N₂S =518.68) Sub 2-68 m/z = 618.21(C₄₄H₃₀N₂S = 618.80) Sub 2-69 m/z =386.18(C₂₈H₂₂N₂ = 386.50) Sub 2-70 m/z = 502.20(C₃₆H₂₆N₂O = 502.62) Sub2-71 m/z = 492.17(C₃₄H₂₄N₂S = 492.64) Sub 2-72 m/z = 437.19(C₃₁H₂₃N₃ =437.55) Sub 2-73 m/z = 462.21(C₃₄H₂₈N₂ = 462.60) Sub 2-74 m/z =372.14(C₂₄H₁₈F₂N₂ = 372.42) Sub 2-75 m/z = 364.19(C₂₆H₂₄N₂ = 364.49) Sub2-76 m/z = 488.23(C₃₆H₂₈N₂ = 488.63) Sub 2-77 m/z = 594.21(C₄₂H₃₀N₂S =594.78) Sub 2-78 m/z = 568.20(C₄₀H₂₈N₂S = 568.74) Sub 2-79 m/z =644.23(C₄₆H₃₂N₂S = 644.84) Sub 2-80 m/z = 568.20(C₄₀H₂₈N₂S = 568.74) Sub2-81 m/z = 492.17(C₃₄H₂₄N₂S = 492.64) Sub 2-82 m/z = 548.14(C₃₆H₂₄N₂S₂ =548.72) Sub 2-83 m/z = 608.19(C₄₂H₂₈N₂SO = 608.76) Sub 2-84 m/z =544.17(C₃₆H₂₄N₄ = 544.68) Sub 2-85 m/z = 680.23(C₄₉H₃₂N₂S = 680.87) Sub2-86 m/z = 732.26(C₅₃H₃₆N₂S = 732.95) Sub 2-87 m/z = 494.18(C₃₄H₂₆N₂S =494.66) Sub 2-88 m/z = 542.18(C₃₈H₂₆N₂S = 542.70) Sub 2-89 m/z =456.17(C₃₁H₂₄N₂S = 456.61) Sub 2-90 m/z = 548.14(C₃₆H₂₄N₂S₂ = 548.72)Sub 2-91 m/z = 426.17(C₃₀H₂₂N₂O = 426.52) Sub 2-92 m/z =578.24(C₄₂H₃₀N₂O = 578.72) Sub 2-93 m/z = 568.20(C₄₀H₂₈N₂S = 568.74) Sub2-94 m/z = 670.24(C₄₈H₃₄N₂S = 670.87)

II. Synthesis of Product

After Sub 1 (1 eq.) was dissolved in toluene in a round bottom flask,Sub 2 (1 eq.), Pd₂(dba)₃ (0.03 eq.), (t-Bu)₃P (0.06 eq.), NaOt-Bu (3eq.) were added to the solution and the mixture was stirred at 120° C.for 3 h. When the reaction was completed, the reaction product wasextracted with CH₂Cl₂ and water, and then the organic layer was driedwith MgSO₄ and concentrated. Then, the concentrate was applied to silicagel column and recrystallized to obtain a final product.

1. Synthesis Example of P-2

After Sub 1-1 (10 g, 28.26 mmol) obtained in the above synthesis wasdissolved in toluene (90 ml) in a round bottom flask, Sub 2-7 (13.07 g,28.26 mmol), Pd₂(dba)₃ (0.98 g, 0.85 mmol), 50% P(t-Bu)₃ (0.68 ml, 1.69mmol), NaOt-Bu (8.15 g, 84.78 mmol) were added to the solution and themixture was stirred at 120° C. When the reaction was completed, thereaction product was extracted with CH₂Cl₂ and water, and then theorganic layer was dried with MgSO₄ and concentrated. Then, theconcentrate was applied to silica gel column and recrystallized toobtain 20 g (yield: 92%) of the product.

2. Synthesis Example of P-14

After Sub 2-40 (13.92 g, 28.26 mmol), Pd₂(dba)₃ (0.98 g, 0.85 mmol), 50%P(t-Bu)₃ (0.68 ml, 1.69 mmol), NaOt-Bu (8.15 g, 84.78 mmol), toluene (90ml) were added to Sub 1-1 (10 g, 28.26 mmol) obtained in the abovesynthesis, 19.5 g (yield: 85%) of the product was obtained by proceedingwith the same method as in synthesis of P-2.

3. Synthesis Example of P-32

After Sub 2-14 (11.8 g, 28.26 mmol), Pd₂(dba)₃ (0.98 g, 0.85 mmol), 50%P(t-Bu)₃ (0.68 ml, 1.69 mmol), NaOt-Bu (8.15 g, 84.78 mmol), toluene (90ml) were added to Sub 1-4 (10 g, 28.26 mmol) obtained in the abovesynthesis, 20 g (yield: 96%) of the product was obtained by proceedingwith the same method as in synthesis of P-2.

4. Synthesis Example of P-46

After Sub 2-45 (12.5 g, 28.26 mmol), Pd₂(dba)₃ (0.98 g, 0.85 mmol), 50%P(t-Bu)₃ (0.68 ml, 1.69 mmol), NaOt-Bu (8.15 g, 84.78 mmol), toluene (90ml) were added to Sub 1-4 (10 g, 28.26 mmol) obtained in the abovesynthesis, 18 g (yield: 84%) of the product was obtained by proceedingwith the same method as in synthesis of P-2.

5. Synthesis Example of P-60

After Sub 2-89 (8 g, 17.39 mmol), Pd₂(dba)₃ (0.5 g, 0.52 mmol), 50%P(t-Bu)₃ (0.42 ml, 1.04 mmol), NaOt-Bu (5 g, 52.18 mmol), toluene (60ml) were added to Sub 1-29 (8 g, 17.39 mmol) obtained in the abovesynthesis, 12 g (yield: 78%) of the product was obtained by proceedingwith the same method as in synthesis of P-2.

6. Synthesis Example of P-68

After Sub 2-66 (14.7 g, 28.26 mmol), Pd₂(dba)₃ (0.98 g, 0.85 mmol), 50%P(t-Bu)₃ (0.68 ml, 1.69 mmol), NaOt-Bu (8.15 g, 84.78 mmol), toluene (90ml) were added to Sub 1-4 (10 g, 28.26 mmol) obtained in the abovesynthesis, 21 g (yield: 89%) of the product was obtained by proceedingwith the same method as in synthesis of P-2.

7. Synthesis Example of P-79

After Sub 2-11 (28.3 g, 58.01 mmol), Pd₂(dba)₃ (2 g, 1.74 mmol), 50%P(t-Bu)₃ (1.4 ml, 3.48 mmol), NaOt-Bu (16.7 g, 174 mmol), toluene (190ml) were added to Sub 1-9 (25 g, 58.01 mmol) obtained in the abovesynthesis, 46 g (yield: 90%) of the product was obtained by proceedingwith the same method as in synthesis of P-2.

8. Synthesis Example of P-96

After Sub 2-58 (12.5 g, 28.26 mmol), Pd₂(dba)₃ (0.98 g, 0.85 mmol), 50%P(t-Bu)₃ (0.68 ml, 1.69 mmol), NaOt-Bu (8.15 g, 84.78 mmol), toluene (90ml) were added to Sub 1-4 (10 g, 28.26 mmol) obtained in the abovesynthesis, 19 g (yield: 89%) of the product was obtained by proceedingwith the same method as in synthesis of P-2.

9. Synthesis Example of P-102

After Sub 2-45 (7.7 g, 17.33 mmol), Pd₂(dba)₃ (0.5 g, 0.52 mmol), 50%P(t-Bu)₃ (0.42 ml, 1.04 mmol), NaOt-Bu (5 g, 51.99 mmol), toluene (60ml) were added to Sub 1-16 (7 g, 17.33 mmol) obtained in the abovesynthesis, 10 g (yield: 72%) of the product was obtained by proceedingwith the same method as in synthesis of P-2.

The FD-MS values of the compounds of the present invention preparedaccording to the above synthesis examples are shown in Table 3 below.

TABLE 3 Compound FD-MS Compound FD-MS P-1 m/z = 653.28(C₄₈H₃₅N₃ =653.83) P-2 m/z = 779.33(C₅₈H₄₁N₃ = 779.99) P-3 m/z = 805.35(C₆₀H₄₃N₃ =806.03) P-4 m/z = 779.33(C₅₈H₄₁N₃ = 779.99) P-5 m/z = 885.32(C₆₄H₄₃N₃S =886.13) P-6 m/z = 759.27(C₅₄H₃₇N₃S = 759.97) P-7 m/z = 833.30(C₆₀H₃₉N₃O₂= 833.99) P-8 m/z = 869.34(C₆₄H₄₃N₃O = 870.07) P-9 m/z = 653.28(C₄₈H₃₅N₃= 653.83) P-10 m/z = 805.35(C₆₀H₄₃N₃ = 806.03) P-11 m/z =835.30(C₆₀H₄₁N₃S = 836.07) P-12 m/z = 961.35(C₇₀H₄₇N₃S = 962.23) P-13m/z = 809.29(C₅₈H₃₉N₃S = 810.03) P-14 m/z = 809.29(C₅₈H₃₉N₃S = 810.03)P-15 m/z = 730.31(C₅₃H₃₈N₄ = 730.92) P-16 m/z = 653.28(C₄₈H₃₅N₃ =653.83) P-17 m/z = 729.31(C₅₄H₃₉N₃ = 729.93) P-18 m/z = 753.31(C₅₆H₃₉N₃= 753.95) P-19 m/z = 865.26(C₆₀H₃₉N₃S₂ = 866.11) P-20 m/z =653.28(C₄₈H₃₅N₃ = 653.83) P-21 m/z = 729.31(C₅₄H₃₉N₃ = 729.93) P-22 m/z= 805.35(C₆₀H₄₃N₃ = 806.03) P-23 m/z = 753.31(C₅₆H₃₉N₃ = 753.95) P-24m/z = 805.35(C₆₀H₄₃N₃ = 806.03) P-25 m/z = 743.29(C₅₄H₃₇N₃O = 743.91)P-26 m/z = 885.32(C₆₄H₄₃N₃S = 886.13) P-27 m/z = 909.32(C₆₆H₄₃N₃S =910.15) P-28 m/z = 653.28(C₄₈H₃₅N₃ = 653.83) P-29 m/z = 729.31(C₅₄H₃₉N₃= 729.93) P-30 m/z = 805.35(C₆₀H₄₃N₃ = 806.03) P-31 m/z =779.33(C₅₈H₄₁N₃ = 779.99) P-32 m/z = 734.35(C₅₄H₃₄D₅N₃ = 734.96) P-33m/z = 829.35(C₆₂H₄₃N₃ = 830.05) P-34 m/z = 823.34(C₆₀H₄₂FN₃ = 824.02)P-35 m/z = 765.30(C₅₄H₃₇F₂N₃ = 765.91) P-36 m/z = 855.36(C₆₄H₄₅N₃ =856.09) P-37 m/z = 845.38(C₆₃H₄₇N₃ = 846.09) P-38 m/z = 941.38(C₇₁H₄₇N₃= 942.18) P-39 m/z = 759.27(C₅₄H₃₇N₃S = 759.97) P-40 m/z =835.30(C₆₀H₄₁N₃S = 836.07) P-41 m/z = 854.31(C₆₀H₃₄D₅N₃OS = 855.08) P-42m/z = 909.37(C₆₇H₄₇N₃O = 910.13) P-43 m/z = 748.33(C₅₄H₃₂D₅N₃O = 748.94)P-44 m/z = 995.39(C₇₄H₄₉N₃O = 996.23) P-45 m/z = 833.30(C₆₀H₃₉N₃O₂ =833.99) P-46 m/z = 759.27(C₅₄H₃₇N₃S = 759.97) P-47 m/z =835.30(C₆₀H₄₁N₃S = 836.07) P-48 m/z = 835.30(C₆₀H₄₁N₃S = 836.07) P-49m/z = 885.32(C₆₄H₄₃N₃S = 886.13) P-50 m/z = 961.35(C₇₀H₄₇N₃S = 962.23)P-51 m/z = 935.33(C₆₈H₄₅N₃S = 936.19) P-52 m/z = 987.36(C₇₂H₄₉N₃S =988.27) P-53 m/z = 885.32(C₆₄H₄₃N₃S = 886.13) P-54 m/z=1053.40(C₇₂H₅₉N₃SSi₂ = 1054.52) P-55 m/z = 836.30(C₅₉H₄₀N₄S = 837.06)P-56 m/z = 1049.38(C₇₇H₅₁N₃S = 1050.34) P-57 m/z = 997.35(C₇₃H₄₇N₃S =998.26) P-58 m/z = 865.26(C₆₀H₃₉N₃S₂ = 866.11) P-59 m/z =925.31(C₆₆H₄₃N₃OS = 926.15) P-60 m/z = 879.27(C₆₁H₄₁N₃S₂ = 880.14) P-61m/z = 937.32(C₆₆H₄₃N₅S = 938.17) P-62 m/z = 835.30(C₆₀H₄₁N₃S = 836.07)P-63 m/z = 865.26(C₆₀H₃₉N₃S₂ = 866.11) P-64 m/z = 987.36(C₇₂H₄₉N₃S =988.27) P-65 m/z = 975.33(C₇₀H₄₅N₃OS = 976.21) P-66 m/z =729.31(C₅₄H₃₉N₃ = 729.93) P-67 m/z = 881.38(C₆₆H₄₇N₃ = 882.12) P-68 m/z= 835.30(C₆₀H₄₁N₃S = 836.07) P-69 m/z = 911.33(C₆₆H₄₅N₃S = 912.17) P-70m/z = 856.36(C₆₃H₄₄N₄ = 857.07) P-71 m/z =1000.36(C₇₂H₄₈N₄S = 1001.26)P-72 m/z = 881.38(C₆₆H₄₇N₃ = 882.12) P-73 m/z = 653.28(C₄₈H₃₅N₃ =653.83) P-74 m/z = 729.31(C₅₄H₃₉N₃ = 729.93) P-75 m/z =935.33(C₆₈H₄₅N₃S936.19) P-76 m/z = 905.38(C₆₈H₄₇N₃ = 906.15) P-77 m/z =653.28(C₄₈H₃₅N₃ = 653.83) P-78 m/z = 729.31(C₅₄H₃₉N₃ = 729.93) P-79 m/z= 882.37(C₆₅H₄₆N₄ = 883.11) P-80 m/z = 759.27(C₅₄H₃₇N₃S = 759.97) P-81m/z = 753.31(C₅₆H₃₉N₃ = 753.95) P-82 m/z = 845.38(C₆₃H₄₇N₃ = 846.09)P-83 m/z = 859.30(C₆₂H₄₁N₃S = 860.09) P-84 m/z = 1041.32(C₇₄H₄₇N₃S₂ =1042.33) P-85 m/z = 805.35(C₆₀H₄₃N₃ = 806.03) P-86 m/z = 805.35(C₆₀H₄₃N₃= 806.03) P-87 m/z = 780.33(C₅₇H₄₀N₄ = 780.98) P-88 m/z =769.35(C₅₇H₄₃N₃ = 769.99) P-89 m/z = 743.29(C₅₄H₃₇N₃O = 743.91) P-90 m/z= 759.27(C₅₄H₃₇N₃S = 759.97) P-91 m/z = 759.27(C₅₄H₃₇N₃S = 759.97) P-92m/z = 759.27(C₅₄H₃₇N₃S = 759.97) P-93 m/z = 835.30(C₆₀H₄₁N₃S = 836.07)P-94 m/z = 835.30(C₆₀H₄₁N₃S = 836.07) P-95 m/z = 865.26(C₆₀H₃₉N₃S₂ =866.11) P-96 m/z = 759.27(C₅₄H₃₇N₃S = 759.97) P-97 m/z =899.30(C₆₄H₄₁N₃OS = 900.11) P-98 m/z = 859.30(C₆₂H₄₁N₃S = 860.09) P-99m/z = 941.29(C₆₆H₄₃N₃S₂ = 942.21) P-100 m/z = 821.38(C₆₁H₄₇N₃ = 822.07)P-101 m/z = 859.30(C₆₂H₄₁N₃S = 860.09) P-102 m/z = 809.29(C₅₈H₃₉N₃S =810.03) P-103 m/z = 904.36(C₆₇H₄₄N₄ = 905.12) P-104 m/z =803.33(C₆₀H₄₁N₃ = 804.01) P-105 m/z = 919.36(C₆₈H₄₅N₃O = 920.13)

In the above, an exemplary synthesis example of the present inventionrepresented by the general formula 1 are described, but all of them arebased on Buchwald-Hartwig cross coupling reaction, Suzuki cross-couplingreaction, Ullmann reaction, Miyaura boration reaction and the like.Therefore, it will be understood by those skilled in the art that theabove reaction proceeds even when other substituents (Ar¹ to Ar⁴, R¹ toR³, L¹, m, n and o) defined in Formula 1 are bonded, in addition to thesubstituents specified in the specific synthesis example.

For example, the reaction of Sub 1 and Sub 2->Final Product in ReactionScheme 1, the reactions of starting materials->Sub 2-I and Sub 2-I->Sub2 in Reaction Scheme 9 are all based on the Buchwald-Hartwig crosscoupling reaction, the reaction of Sub 1-II->Sub 1 in Reaction Scheme 2is based on the Suzuki cross-coupling reaction, the reaction of startingmaterials->Sub 1-1 in Reaction Scheme 3 is based on the Ullmannreaction, and the reaction of Sub 1-I->Sub 1-II in Reaction Scheme 3 isbased on the Miyaura boration reaction. The above reactions will proceedeven if a substituent not specifically mentioned is attached.

Fabrication and Evaluation of Organic Electronic Element

[Example 1] Red OLED (an Emission-Auxiliary Layer)

Organic light emitting diode (OLED) was fabricated according to aconventional method by using a compound of the present invention as anemission-auxiliary layer material. First, an ITO layer (anode) wasformed on a glass substrate, and then4,4′,4″-tris[2-naphthyl(phenyl)amino]triphenylamine (hereinafter,“2-TNATA”) was vacuum-deposited on the ITO layer to form a holeinjection layer with a thickness of 60 nm.

Subsequently, 4,4′-bis[N-(1-napthyl)-N-phenyl-amino] biphenyl(hereinafter, “NPD”) was vacuum-deposited with a thickness of 60 nm onthe hole injection layer to form a hole transport layer. Subsequently, afilm of the compound P-1 of the present invention was vacuum-depositedon the hole transport layer to form an emission-auxiliary layer with athickness of 20 nm. A light emitting layer with a thickness of 30 nm wasdeposited on the emission-auxiliary layer by using4,4′-N,N′-dicarbazole-biphenyl (hereinafter, “CBP”) as a host materialand bis-(1-phenylisoquinoline)iridium(III)acetylacetonate (hereinafter,“(piq)₂Ir(acac)”) as a dopant material in a weight ratio of 95:5. Next,a film of (1,1′-biphenyl-4-olato)bis(2-methyl-8-quinolinolato)aluminum(hereinafter, “BAlq”) was vacuum-deposited with a thickness of 5 nm onthe light emitting layer to form a hole blocking layer, and a film ofBis(10-hydroxybenzo[h]quinolinato)berylium (hereinafter, “BeBq₂”) wasformed with a thickness of 40 nm to form an electron transport layer.

Next, LiF as halogenated alkali metal was deposited with a thickness of0.2 nm on the electron transport layer to form an electron injectionlayer, and then Al was deposited with a thickness of 150 nm on theelectron injection layer to form a cathode. In this way, the OLED wascompleted.

[Example 2] to [Example 50] Red OLED (an Emission-Auxiliary Layer)

The OLEDs were fabricated in the same manner as described in Example 1except that the compounds of the present invention described in thefollowing Table 4, instead of the compound P-1 of the present invention,were used as an emission-auxiliary layer material.

Comparative Example 1

The OLED was fabricated in the same manner as described in Example 1except that an emission-auxiliary layer was not formed.

[Comparative Example 2] to [Comparative Example 6] Red OLED (anEmission-Auxiliary Layer)

The OLEDs were fabricated in the same manner as described in Example 1except that the Comparative compounds 1 to 5 described in the followingTable 4, instead of the compound P-1 of the present invention, were usedas an emission-auxiliary layer material.

Electroluminescence (EL) characteristics were measured with a PR-650(Photoresearch) by applying a forward bias DC voltage to the OLEDsprepared in Examples 1 to 50 of the present invention and ComparativeExamples 1 to 6. And, the T95 life time was measured using a life timemeasuring apparatus manufactured by Macscience Inc. at referencebrightness of 2500 cd/m². The measurement results are shown in Tables 4below.

TABLE 4 Current Voltage Density Brightness Efficiency Lifetime CIECompound (V) (mA/cm²) (cd/m²) (cd/A) T(95) x y comp. Ex(1) — 5.3 33.32500 7.5 62.7 0.66 0.32 comp. Ex(2) comp. Com1 5.7 30.9 2500 8.1 72.20.66 0.32 comp. Ex(3) comp. Com2 5.8 26.6 2500 9.4 75.4 0.66 0.33 comp.Ex(4) comp. Com3 5.7 24.5 2500 10.2 79.8 0.66 0.33 comp. Ex(5) comp.Com4 5.7 20.8 2500 12.0 85.9 0.66 0.33 comp. Ex(6) comp. Com5 5.6 19.12500 13.1 91.2 0.66 0.32 Ex.(1) Com.(P-1) 5.6 13.9 2500 18.0 120.5 0.660.32 Ex.(2) Com.(P-2) 5.6 13.4 2500 18.7 127.3 0.66 0.32 Ex.(3)Com.(P-5) 5.5 12.6 2500 19.8 130.5 0.66 0.32 Ex.(4) Com.(P-6) 5.5 13.02500 19.2 131.5 0.66 0.32 Ex.(5) Com.(P-8) 5.6 13.0 2500 19.2 131.9 0.660.33 Ex.(6) Com.(P-9) 5.5 12.4 2500 20.1 134.0 0.66 0.33 Ex.(7)Com.(P-12) 5.4 12.0 2500 20.8 133.8 0.66 0.32 Ex.(8) Com.(P-14) 5.5 11.92500 21.0 136.2 0.66 0.32 Ex.(9) Com.(P-16) 5.5 12.3 2500 20.3 134.60.66 0.33 Ex.(10) Com.(P-20) 5.4 11.5 2500 21.7 136.5 0.66 0.32 Ex.(11)Com.(P-21) 5.4 11.6 2500 21.5 136.2 0.66 0.33 Ex.(12) Com.(P-25) 5.411.1 2500 22.6 138.7 0.66 0.33 Ex.(13) Com.(P-26) 5.5 11.4 2500 21.9139.9 0.66 0.32 Ex.(14) Com.(P-28) 5.5 10.5 2500 23.7 140.9 0.66 0.33Ex.(15) Com.(P-30) 5.4 10.5 2500 23.9 142.9 0.66 0.33 Ex.(16) Com.(P-32)5.5 10.5 2500 23.8 144.5 0.66 0.32 Ex.(17) Com.(P-37) 5.5 10.7 2500 23.3138.3 0.66 0.33 Ex.(18) Com.(P-38) 5.4 10.6 2500 23.5 138.7 0.66 0.33Ex.(19) Com.(P-39) 5.4 10.3 2500 24.4 143.9 0.66 0.33 Ex.(20) Com.(P-40)5.5 10.3 2500 24.2 144.4 0.66 0.32 Ex.(21) Com.(P-41) 5.4 10.4 2500 24.1143.4 0.66 0.32 Ex.(22) Com.(P-42) 5.4 10.4 2500 24.0 143.4 0.66 0.33Ex.(23) Com.(P-43) 5.4 10.1 2500 24.7 149.9 0.66 0.32 Ex.(24) Com.(P-46)5.3 9.7 2500 25.9 165.1 0.66 0.33 Ex.(25) Com.(P-47) 5.3 9.8 2500 25.6157.6 0.66 0.32 Ex.(26) Com.(P-48) 5.3 9.8 2500 25.6 157.7 0.66 0.32Ex.(27) Com.(P-49) 5.3 10.0 2500 25.0 147.3 0.66 0.33 Ex.(28) Com.(P-53)5.3 10.0 2500 25.1 150.5 0.66 0.32 Ex.(29) Com.(P-58) 5.4 10.1 2500 24.8151.7 0.66 0.33 Ex.(30) Com.(P-60) 5.3 10.1 2500 24.8 150.1 0.66 0.32Ex.(31) Com.(P-62) 5.3 10.0 2500 25.0 150.5 0.66 0.33 Ex.(32) Com.(P-66)5.4 10.7 2500 23.3 139.9 0.66 0.32 Ex.(33) Com.(P-68) 5.5 10.3 2500 24.3143.5 0.66 0.32 Ex.(34) Com.(P-69) 5.4 10.5 2500 23.8 142.9 0.66 0.33Ex.(35) Com.(P-73) 5.4 10.9 2500 22.9 137.9 0.66 0.33 Ex.(36) Com.(P-75)5.4 10.9 2500 22.9 137.8 0.66 0.33 Ex.(37) Com.(P-77) 5.6 13.4 2500 18.7122.7 0.66 0.33 Ex.(38) Com.(P-78) 5.6 13.0 2500 19.3 132.3 0.66 0.33Ex.(39) Com.(P-85) 5.6 13.3 2500 18.8 126.6 0.66 0.33 Ex.(40) Com.(P-88)5.6 13.7 2500 18.3 122.2 0.66 0.33 Ex.(41) Com.(P-89) 5.5 12.2 2500 20.5134.6 0.66 0.33 Ex.(42) Com.(P-90) 5.4 11.8 2500 21.1 136.9 0.66 0.33Ex.(43) Com.(P-92) 5.3 9.6 2500 26.1 164.4 0.66 0.32 Ex.(44) Com.(P-93)5.3 9.8 2500 25.6 155.4 0.66 0.33 Ex.(45) Com.(P-94) 5.3 9.8 2500 25.5158.5 0.66 0.32 Ex.(46) Com.(P-95) 5.4 10.3 2500 24.4 144.4 0.66 0.33Ex.(47) Com.(P-96) 5.4 9.9 2500 25.2 151.8 0.66 0.32 Ex.(48) Com.(P-99)5.4 10.3 2500 24.2 143.8 0.66 0.33 Ex.(49) Com.(P-102) 5.4 10.1 250024.7 147.4 0.66 0.33 Ex.(50) Com.(P-105) 5.5 10.9 2500 22.9 137.6 0.660.32

From the Table 4, it can be seen that the luminous efficiency andlifetime of the organic electroluminescent device are remarkablyimproved when compounds of the present invention were used as anemission-auxiliary layer material, compared Comparative Examples 1 to 6.That is, the organic electroluminescent devices employing theComparative compounds 1 to 5, or the compounds of the present inventionshowed the improved luminous efficiency and lifetime, compared to theorganic electroluminescent device not comprising an emission-auxiliarylayer, and among them, the cases where the compounds of the presentinvention were used showed remarkably improved luminous efficiency andlifetime.

In particular, comparing the cases where the Comparative compounds 1 and2 were used with the cases where the compounds of the present inventionwere used, it is confirmed that there is a large difference in luminousefficiency and lifetime depending on whether the linker connecting thecarbazole core and the amine type (—N(Ar²)-L¹-N(Ar³)(Ar⁴)) is introducedor not and where the linker is bonded, even if the same amine type(—N(Ar²)-L¹-N(Ar³)(Ar⁴)) is bonded to the carbazole core. This isbecause the case where the linker is introduced between the carbazolecore and the amine type (—N(Ar²)-L¹-N(Ar³)(Ar⁴)) has a deeper HOM energylevel than when the carbazole core and the amine type(—N(Ar²)-L-N(Ar³)(Ar⁴)) are directly bonded without the linker and thusthe charge balance of holes and electrons in the light emitting layer isincreased as the hole can move more easily.

In addition, the compound of the present invention in which the linkeris directly bonded to at the 2-position of the carbazole backbone has ashorter conjugation length than the Comparative compound 2 bonded to atthe 3-position of the carbazole core, as a result, it can be seen thatthe band gap is widened, HOMO energy level is deepened and the value ofT1 is increased.

The results depending on the number of cores or the type of theintroduced atoms (N, O) on the same skeleton can be confirmed bycomparing the compounds of the present invention with ComparativeCompounds 3 to 5. The case where two or more carbazole cores areintroduced as in Comparative Compound 5, or the case where dibenzofuranin place of carbazole is introduced as the core has a relatively low T1value as compared with the compound of the present invention. As aresult, it is confirmed that the luminous efficiency and lifetime arereduced by decreasing the ability to block electrons.

Among the compounds of the present invention, comparing the compound P-1(linear type in which carbazole and amine are bonded at the paraposition of phenyl being a liker) of the present invention and thecompound P-20 (non-linear type in which carbazole and amine are bondedat the meta position of phenyl being a liker), it shows differentresults depending on the linking type (linear type or nonlinear type) ofthe linker.

The case where the carbazole core and the amine type(—N(Ar²)-L¹-N(Ar³)(Ar⁴)) are bonded to the linker at the meta-position,that is non-linear type, showed deeper HOMO energy level and higher T1value than the case where the carbazole core and the amine type(—N(Ar²)-L¹-N(Ar³)(Ar⁴)) are bonded to the linker at the para-position,that is linear type. This shows that the compound P-20 of the presentinvention is improved in driving voltage, luminous efficiency andlifetime as compared with the compound P-1 of the present invention.

In addition, among the compounds of the present invention, when at leastone heterocyclic substituent such as a dibenzothiophene is introduced asa substituent of an amine, the refractive index increases and the Tgvalue increases, comparing to the case where aryl groups are allintroduced as a substituents of an amine. As a result, it can be seenthat the luminous efficiency and thermal stability were improved.

In the evaluation results of the above-described device fabrication, thedevice characteristics has been described when the compound of thepresent invention is applied to only one of the hole transport layer andan emission-auxiliary layer. However, the compounds of the presentinvention can be used for both the hole transport layer and anemission-auxiliary layer.

Although exemplary embodiments of the present invention have beendescribed for illustrative purposes, those skilled in the art willappreciate that various modifications, additions and substitutions arepossible, without departing from the scope and spirit of the inventionas disclosed in the accompanying claims. Therefore, the embodimentdisclosed in the present invention is intended to illustrate the scopeof the technical idea of the present invention, and the scope of thepresent invention is not limited by the embodiment. The scope of thepresent invention shall be construed on the basis of the accompanyingclaims, and it shall be construed that all of the technical ideasincluded within the scope equivalent to the claims belong to the presentinvention.

The invention claimed is:
 1. A compound of Formula 1:

wherein: Ar¹ to Ar⁴ are each independently selected from the groupconsisting of a C₆-C₆₀ aryl group, a C₂-C₆₀ heterocyclic groupcontaining at least one heteroatom selected from the group consisting ofO, N, S, Si, and P, a fluorenyl group, a fused ring group of a C₃-C₆₀aliphatic ring and a C₆-C₆₀ aromatic ring, a C₁-C₅₀ alkyl group, aC₂-C₂₀ alkenyl group, a C₂-C₂₀ alkynyl group, a C₁-C₃₀ alkoxyl group anda C₆-C₃₀ aryloxy group, with the proviso that a triphenylene group isexcluded from Ar² and a carbazole group is excluded from Ar³ and Ar⁴, R¹to R³ are each independently selected from the group consisting ofdeuterium, tritium, halogen, a cyano group, a nitro group, a C₆-C₆₀ arylgroup, a fluorenyl group, a C₂-C₆₀ heterocyclic group containing atleast one heteroatom selected from the group consisting of O, N, S, Si,and P, a fused ring group of a C₃-C₆₀ aliphatic ring and a C₆-C₆₀aromatic ring, a C₁-C₅₀ alkyl group, a C₂-C₂₀ alkenyl group, a C₂-C₂₀alkynyl group, a C₁-C₃₀ alkoxyl group and a C₆-C₃₀ aryloxy group, m isan integer of 0, or 2 to 4, n is an integer of 0, 2 or 3, o is 0, andadjacent R¹s or adjacent R²s are linked together to form at least onemonocyclic ring when m or n is each an integer of 2 or more, L¹ isselected from the group consisting of a C₆-C₆₀ arylene group, afluorenylene group, a C₂-C₆₀ heterocyclic group containing at least oneheteroatom selected from the group consisting of O, N, S, Si, and P, afused ring group of a C₃-C₆₀ aliphatic ring and a C₆-C₆₀ aromatic ring,and an aliphatic hydrocarbon group, and the aryl group, arylene group,fluorenyl group, fluorenylene group, heterocyclic group, fused ringgroup, alkyl group, alkenyl group, alkynyl group, alkoxyl group andaryloxyl group of Ar¹ to Ar⁴, R¹ to R³ and L¹ are each optionallyfurther substituted with one or more substituents selected from thegroup consisting of deuterium, halogen, a silane group substituted orunsubstituted with C₁-C₂₀ alkyl group or C₆-C₂₀ aryl group, a siloxanegroup, a boron group, a germanium group, a cyano group, a nitro group, aC₁-C₂₀ alkylthio group, a C₁-C₂₀ alkoxyl group, a C₁-C₂₀ alkyl group, aC₂-C₂₀ alkenyl group, a C₂-C₂₀ alkynyl group, a C₆-C₂₀ aryl group, aC₆-C₂₀ aryl group substituted with deuterium, a fluorenyl group, aC₂-C₂₀ heterocyclic group containing at least one heteroatom selectedfrom the group consisting of O, N, S, Si, and P, a C₃-C₂₀ cycloalkylgroup, a C₇-C₂₀ arylalkyl group and a C₈-C₂₀ arylalkenyl group, whereinadjacent substituents may optionally be linked together to form a ring,with the proviso that where an aryl group of Ar² to Ar⁴ is substitutedwith a heterocyclic group, a carbazole, a dibenzothienyl group or adibenzofuryl group is excluded from the heterocyclic group.
 2. Thecompound of claim 1, wherein Formula 1 is represented by one of thefollowing Formulas 2 to 4:

wherein Ar¹ to Ar⁴, R¹ to R³, L¹, m, n and o are the same as defined inclaim
 1. 3. The compound of claim 1, wherein L¹ 1 is represented by oneof the following Formulas L1-1 to L1-7:

wherein: X is S, O, C(R^(a))(R^(b)) or N(R^(c)), wherein R^(a), R^(b)and R^(c) are each independently selected from the group consisting of aC₆-C₂₀ aryl group, a fluorenyl group, a C₂-C₂₀ heterocyclic groupcontaining at least one heteroatom selected from the group consisting ofO, N, S, Si, and P, a fused ring group of a C₃-C₂₀ aliphatic ring and aC₆-C₆₀ aromatic ring, a C₁-C₂₀ alkyl group, a C₂-C₂₀ alkenyl group, aC₂-C₂₀ alkynyl group, a C₁-C₃₀ alkoxyl group and a C₆-C₃₀ aryloxy group,and R^(a) and R^(b) may optionally be linked together to form a spirocompound together with a carbon to which they are bonded, R⁴ and R⁵ areeach independently selected from the group consisting of a C₆-C₂₀ arylgroup, a fluorenyl group, a C₂-C₂₀ heterocyclic group containing atleast one heteroatom selected from the group consisting of O, N, S, Si,and P, a fused ring group of a C₃-C₂₀ aliphatic ring and a C₆-C₆₀aromatic ring, a C₁-C₂₀ alkyl group, a C₂-C₂₀ alkenyl group, a C₂-C₂₀alkynyl group, a C₁-C₃₀ alkoxyl group and a C₆-C₃₀ aryloxy group, and ato b are each an integer of 0 to 4, c is an integer of 0 to 6, d is aninteger of 0 to 5, e and f are each an integer of 0 to 3, and each ofthe plurality of R⁴s and each of the plurality of R⁵s are the same ordifferent from each other where a, b, c, d, e and f are each an integerof 2 or more.
 4. A compound of Formula 1:

wherein: Ar¹ to Ar⁴ are each independently selected from the groupconsisting of a C₆-C₆₀ aryl group, a C₂-C₆₀ heterocyclic groupcontaining at least one heteroatom selected from the group consisting ofO, N, S, Si, and P, a fluorenyl group, a fused ring group of a C₃-C₆₀aliphatic ring and a C₆-C₆₀ aromatic ring, a C₁-C₅₀ alkyl group, aC₂-C₂₀ alkenyl group, a C₂-C₂₀ alkynyl group, a C₁-C₃₀ alkoxyl group anda C₆-C₃₀ aryloxy group, with the proviso that a triphenylene group isexcluded from Ar² and a carbazole group is excluded from Ar³ and Ar⁴, R¹to R³ are each independently selected from the group consisting ofdeuterium, tritium, halogen, a cyano group, a nitro group, a C₆-C₆₀ arylgroup, a fluorenyl group, a C₂-C₆₀ heterocyclic group containing atleast one heteroatom selected from the group consisting of O, N, S, Si,and P, a fused ring group of a C₃-C₆₀ aliphatic ring and a C₆-C₆₀aromatic ring, a C₁-C₅₀ alkyl group, a C₂-C₂₀ alkenyl group, a C₂-C₂₀alkynyl group, a C₁-C₃₀ alkoxyl group and a C₆-C₃₀ aryloxy group, m ando are each an integer of 0 to 4, n is an integer of 0 to 3 and adjacentR¹s, adjacent R²s or adjacent R³s may optionally be linked together toform a ring when m, n or o is each an integer of 2 or more, L¹ isselected from the group consisting of a C₆-C₆₀ arylene group, afluorenylene group, a C₂-C₆₀ heterocyclic group containing at least oneheteroatom selected from the group consisting of O, N, S, Si, and P, afused ring group of a C₃-C₆₀ aliphatic ring and a C₆-C₆₀ aromatic ring,and an aliphatic hydrocarbon group, and the aryl group, arylene group,fluorenyl group, fluorenylene group, heterocyclic group, fused ringgroup, alkyl group, alkenyl group, alkynyl group, alkoxyl group andaryloxyl group of Ar¹ to Ar⁴, R¹ to R³ and L¹ are each optionallyfurther substituted with one or more substituents selected from thegroup consisting of deuterium, halogen, a silane group substituted orunsubstituted with C₁-C₂₀ alkyl group or C₆-C₂₀ aryl group, a siloxanegroup, a boron group, a germanium group, a cyano group, a nitro group, aC₁-C₂₀ alkylthio group, a C₁-C₂₀ alkoxyl group, a C₁-C₂₀ alkyl group, aC2-C₂₀ alkenyl group, a C₂-C₂₀ alkynyl group, a C₆-C₂₀ aryl group, aC₆-C₂₀ aryl group substituted with deuterium, a fluorenyl group, aC₂-C₂₀ heterocyclic group containing at least one heteroatom selectedfrom the group consisting of O, N, S, Si, and P, a C₃-C₂₀ cycloalkylgroup, a C₇-C₂₀ arylalkyl group and a C₈-C₂₀ arylalkenyl group, whereinadjacent substituents may optionally be linked together to form a ring,with the proviso that where an aryl group of Ar² to Ar⁴ is substitutedwith a heterocyclic group, a carbazole, a dibenzothienyl group or adibenzofuryl group is excluded from the heterocyclic group, wherein atleast one of Ar¹ to Ar⁴ is represented by the following Formula 5:

wherein: Y is S, O or C(R^(d))(R^(e)), wherein R^(d) and R^(e) are eachindependently selected from the group consisting of a C₆-C₂₀ aryl group,a fluorenyl group, a C₂-C₂₀ heterocyclic group containing at least oneheteroatom selected from the group consisting of O, N, S, Si, and P, afused ring group of a C₃-C₂₀ aliphatic ring and a C₆-C₂₀ aromatic ring,a C₁-C₂₀ alkyl group, a C₂-C₂₀ alkenyl group, a C₂-C₂₀ alkynyl group, aC₁-C₃₀ alkoxyl group and a C₆-C₃₀ aryloxy group, R⁶ and R⁷ are eachindependently selected from the group consisting of a C₆-C₂₀ aryl group,a fluorenyl group, a C₂-C₂₀ heterocyclic group containing at least oneheteroatom selected from the group consisting of O, N, S, Si, and P, afused ring group of a C₃-C₂₀ aliphatic ring and a C₆-C₂₀ aromatic ring,a C₁-C₂₀ alkyl group, a C₂-C₂₀ alkenyl group, a C₂-C₂₀ alkynyl group, aC₁-C₃₀ alkoxyl group and a C₆-C₃₀ aryloxy group, h is an integer of 0 to4, g is an integer of 0 to 3, and plural R⁶s and plural R⁷s are each thesame or different from each other where h and g are each an integer of 2or more.
 5. The compound of claim 4, wherein at least one of Ar¹ to Ar⁴in the formula 1 is the formula 5 and Y in the formula 5 is S.
 6. Acompound selected from compounds P-1 to p-105


7. An organic electric element comprising a first electrode, a secondelectrode, and an organic material layer formed between the firstelectrode and the second electrode, wherein the organic material layercomprises the compound of claim
 1. 8. The organic electric element ofclaim 7, wherein the compound is comprised in at least one layer of ahole injection layer, one or more hole transport layer, anemission-auxiliary layer, a light emitting layer, an electron transportauxiliary layer, one or more electron transport layer and an electroninjection layer of the organic material layer, and the compound iscomprised as a single compound or a mixture of two or more kinds in theorganic material layer.
 9. The organic electric element of claim 8,wherein the compound is comprised in one or more hole transport layer orone or more the emission-auxiliary layer.
 10. The organic electricelement of claim 7, wherein the organic material layer is formed by aprocess of spin coating, nozzle printing, inkjet printing, slot coating,dip coating or roll-to-roll.
 11. An electronic device comprising adisplay device and a control unit for driving the display device,wherein the display device comprises the organic electric element ofclaim
 7. 12. The electronic device of claim 11, wherein the organicelectric element is one of an organic light emitting diode, an organicsolar cell, an organic photo conductor, an organic transistor, and anelement for monochromatic or white illumination.
 13. An organic electricelement comprising a first electrode, a second electrode, and an organicmaterial layer formed between the first electrode and the secondelectrode, wherein the organic material layer comprises the compound ofclaim
 4. 14. The organic electric element of claim 13, wherein thecompound is comprised in at least one layer of a hole injection layer,one or more hole transport layer, an emission-auxiliary layer, a lightemitting layer, an electron transport auxiliary layer, one or moreelectron transport layer and an electron injection layer of the organicmaterial layer, and the compound is comprised as a single compound or amixture of two or more kinds in the organic material layer.
 15. Anelectronic device comprising a display device and a control unit fordriving the display device, wherein the display device comprises theorganic electric element of claim
 13. 16. The electronic device of claim15, wherein the organic electric element is one of an organic lightemitting diode, an organic solar cell, an organic photo conductor, anorganic transistor, and an element for monochromatic or whiteillumination.
 17. An organic electric element comprising a firstelectrode, a second electrode, and an organic material layer formedbetween the first electrode and the second electrode, wherein theorganic material layer comprises the compound of claim
 6. 18. Theorganic electric element of claim 17, wherein the compound is comprisedin at least one layer of a hole injection layer, one or more holetransport layer, an emission-auxiliary layer, a light emitting layer, anelectron transport auxiliary layer, one or more electron transport layerand an electron injection layer of the organic material layer, and thecompound is comprised as a single compound or a mixture of two or morekinds in the organic material layer.
 19. An electronic device comprisinga display device and a control unit for driving the display device,wherein the display device comprises the organic electric element ofclaim
 17. 20. The electronic device of claim 19, wherein the organicelectric element is one of an organic light emitting diode, an organicsolar cell, an organic photo conductor, an organic transistor, and anelement for monochromatic or white illumination.